Number 69 - American Chemical Society

Jul 3, 2003 - Department of Chemistry, Reedley College, 339 West Carpenter Avenue, Reedley, California 93654 [email protected]. Reviews are listed ...
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Number 69 compiled by Veronica M. Cornel Department of Chemistry, Reedley College, 339 West Carpenter Avenue, Reedley, California 93654 [email protected]

Reviews are listed in order of appearance in the sources indicated. In multidisciplinary review journals, only those reviews which fall within the scope of this Journal are included. Sources are listed alphabetically in three categories: regularly issued review journals and series volumes, contributed volumes, and other monographs. Titles are numbered serially, and these numbers are used for reference in the index. Major English-language sources of critical reviews are covered. Encyclopedic treatises, annual surveys such as Specialist Periodical Reports, and compilations of symposia proceedings are omitted. This installment of Recent Reviews covers principally the early part of the 2003 literature. Previous installment: J. Org. Chem. 2003, 68(7), 2987-96. Supporting Information Available: A file containing this Recent Review compilation in Microsoft Word and the data in rtf format. This material is available free of charge via the Internet at http://pubs.acs.org.

Regularly Issued Journals and Series Volumes Accounts of Chemical Research 1. Pamplin, C. B.; Legzdins, P. Thermal Activation of Hydrocarbon C-H Bonds by Cp*M(NO) Complexes of Molybdenum and Tungsten. 2003, 36(4), 223-33. 2. Culkin, D. A.; Hartwig, J. F. Palladium-Catalyzed R-Arylation of Carbonyl Compounds and Nitriles. 2003, 36(4), 234-45. 3. Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules. 2003, 36(4), 255-63. 4. Breit, B. Synthetic Aspects of Stereoselective Hydroformylation. 2003, 36(4), 264-75. 5. Tius, M. A. Cationic Cyclopentannelation of Allene Ethers. 2003, 36(4), 284-90. 6. Kotha, S. The Building Block Approach to Unusual R-Amino Acid Derivatives and Peptides. 2003, 36(5), 342-51. Advanced Synthesis and Catalysis 7. Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines. 2002, 344(8), 795-813. 8. Saluzzo, C.; Lemaire, M. Homogeneous-Supported Catalysts for Enantioselective Hydrogenation and Hydrogen Transfer Reduction. 2002, 344(9), 915-28. 9. Gomez, S.; Peters, J. A.; Maschmeyer, T. The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control. 2002, 344(10), 1037-57.

10. Nilov, D.; Reiser, O. The Sharpless Asymmetric Aminohydroxylation-Scope and Limitation. 2002, 344(10), 1169-73. Advances in Heterocyclic Chemistry 11. Vasilevsky, S. F.; Tretyakov, E. V.; Elguero, J. Synthesis and Properties of Acetylenic Derivatives of Pyrazoles. 2002, 82, 1-99. 12. Somei, M. Recent Advances in the Chemistry of 1-Hydroxyindoles, 1- Hydroxytryptophans, and 1-Hydroxytryptamines. 2002, 82, 101-55. 13. Kozhevnikov, D. N.; Rusinov, V. L.; Chupakhin, O. N. 1,2,4-Triazine N-Oxides. 2002, 82, 261-305. Advances in Physical Organic Chemistry 14. Abboud, J.-L. M.; Alkorta, I.; Davalos, J. Z.; Muller, P.; Quintanilla, E. Thermodynamic Stabilities of Carbocations. 2002, 37, 57-135. 15. Bernasconi, C. F. The Physical Organic Chemistry of Fischer Carbene Complexes. 2002, 37, 137-237. Angewandte Chemie, International Edition in English 16. Kimball, D. B.; Haley, M. M. Triazenes: A Versatile Tool in Organic Synthesis. 2002, 41(18), 3338-51. 17. Mikami, K.; Terada, M.; Matsuzawa, H. “Asymmetric” Catalysis by Lanthanide Complexes. 2002, 41(19), 3554-71.

10.1021/jo033582m CCC: $25.00 © 2003 American Chemical Society

Published on Web 07/03/2003

J. Org. Chem. 2003, 68, 5795-5804

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18. Goossen, L. J. Asymmetric Hydrovinylation: New Perspectives Through use of Modular Ligand Systems. 2002, 41(20), 3775-8. 19. Tzschucke, C. C.; Markert, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Modern Separation Techniques for Efficient Workup in Organic Synthesis. 2002, 41(21), 3964-4000. 20. Bodwell, G. J.; Satou, T. “Polyunsaturated” Cyclophanes. 2002, 41(21), 4003-6. 21. Littke, A. F.; Fu, G. C. Palladium-Catalyzed Coupling Reactions of Aryl Chlorides. 2002, 41(22), 4176-211. 22. Wadepohl, H. Hypoelectronic Dimetallaboranes. 2002, 41(22), 4220-3. 23. Bera, J. K.; Dunbar, K. R. Chain Compounds Based on Transition Metal Backbones: New Life for an Old Topic. 2002, 41(23), 4453-7. 24. Yeung, K.-S.; Paterson, I. Actin-Binding Marine Macrolides: Total Synthesis and Biological Importance. 2002, 41(24), 4632-53. 25. Miller, J. S. Bistable Electrical, Optical, and Magnetic Behavior in a Molecule-Based Material. 2003, 42(1), 27-9. 26. Lin, H.; Danishefsky, S. J. Gelsemine: A ThoughtProvoking Target for Total Synthesis. 2003, 42(1), 3651. 27. Dzyuba, S. V.; Bartsch, R. A. Recent Advances in Applications of Room-Temperature Ionic Liquid/Supercritical CO2 Systems. 2003, 42(2), 148-50. 28. Coperet, C.; Chabanas, M.; Saint-Arroman, R. P.; Basset, J.-M. Homogeneous and Heterogeneous Catalysis: Bridging the Gap through Surface Organometallic Chemistry. 2003, 42(2), 156-81. Australian Journal of Chemistry 29. Gathergood, N. Asymmetric Organocatalysis: Proline an Essential Amino Acid? 2002, 55(9), 615. 30. Bourgeois, J.-P.; Fujita, M. Chemical Transformations within Isolated Nanospaces. 2002, 55(10), 619-21. 31. Yasui, Y. [V2Cl3(THF)6]2[Zn2Cl6]: Reagent for Highly Selective Pinacol-Coupling Reactions. 2002, 55(10), 685.

38. Power, P. P. Persistent and Stable Radicals of the Heavier Main Group Elements and Related Species. 2003, 103(3), 789-809. 39. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Recent Advances in the Baylis-Hillman Reaction and Applications. 2003, 103(3), 811-91. 40. Horton, D. A.; Bourne, G. T.; Smythe, M. L. The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. 2003, 103(3), 893-930. 41. Rademacher, P. Photoelectron Spectra of Cyclopropane and Cyclopropene Compounds. 2003, 103(4), 933-75. 42. Pietruszka, J. Synthesis and Properties of Oligocyclopropyl-Containing Natural Products and Model Compounds. 2003, 103(4), 1051-70. 43. Dolbier, W. R., Jr.; Battiste, M. A. Structure, Synthesis, and Chemical Reactions of Fluorinated Cyclopropanes and Cyclopropenes. 2003, 103(4), 1071-98. 44. Fedorynski, M. Syntheses of gem-Dihalocyclopropanes and Their Use in Organic Synthesis. 2003, 103(4), 1099-132. 45. Sydnes, L. K. Allenes from Cyclopropanes and Their Use in Organic Synthesis-Recent Developments. 2003, 103(4), 1133-50. 46. Reissig, H.-U.; Zimmer, R. Donor-Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic Synthesis. 2003, 103(4), 1151-96. 47. Baldwin, J. E. Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes. 2003, 103(4), 1197-212. 48. Baird, M. S. Thermally Induced CyclopropeneCarbene Rearrangements: An Overview. 2003, 103(4), 1271-94. 49. Nakamura, M.; Isobe, H.; Nakamura, E. Cyclopropenone AcetalssSynthesis and Reactions. 2003, 103(4), 1295-326. 50. Halton, B. Cycloproparenes. 2003, 103(4), 132769. 51. Sekiguchi, A.; Lee, V. Y. Heavy Cyclopropenes of Si, Ge, and SnsA New Challenge in the Chemistry of Group 14 Elements. 2003, 103(4), 1429-47. Chemical Society Reviews

Chemical Reviews 32. Bordusa, F. Proteases in Organic Synthesis. 2002, 102(12), 4817-67. 33. Uma, R.; Crevisy, C.; Gree, R. Transposition of Allylic Alcohols into Carbonyl Compounds Mediated by Transition Metal Complexes. 2003, 103(1), 27-51. 34. Rossi, R. A.; Pierini, A. B.; Penenory, A. B. Nucleophilic Substitution Reactions by Electron Transfer. 2003, 103(1), 71-167. 35. Fagnou, K.; Lautens, M. Rhodium-Catalyzed Carbon-Carbon Bond Forming Reactions of Organometallic Compounds. 2003, 103(1), 169-96. 36. Jagodzinski, T. S. Thioamides as Useful Synthons in the Synthesis of Heterocycles. 2003, 103(1), 197-227. 37. Dilman, A. D.; Ioffe, S. L. Carbon-Carbon Bond Forming Reactions Mediated by Silicon Lewis Acids. 2003, 103(3), 733-72. 5796 J. Org. Chem., Vol. 68, No. 14, 2003

52. Sweeney, J. B. Aziridines: Epoxides’ Ugly Cousins? 2002, 31(5), 247-58. 53. Ansell, J.; Wills, M. Enantioselective Catalysis Using Phosphorus-Donor Ligands Containing Two or Three P-N or P-O Bonds. 2002, 31(5), 259-68. 54. Brocklehurst, B. Magnetic Fields and Radical Reactions: Recent Developments and Their Role in Nature. 2002, 31(5), 301-11. 55. Perez-Garcia, L.; Amabilino, D. B. Spontaneous Resolution under Supramolecular Control. 2002, 31(6), 342-56. 56. Dehli, J. R.; Gotor, V. Parallel Kinetic Resolution of Racemic Mixtures: A New Strategy for the Preparation of Enantiopure Compounds? 2002, 31(6), 365-70. 57. Poli, R.; Harvey, J. N. Spin Forbidden Chemical Reactions of Transition Metal Compounds. New Ideas and New Computational Challenges. 2003, 32(1), 1-8.

58. Neumueller, B. Organometallic Sesquialkoxides of Aluminium, Gallium and Indium. 2003, 32(1), 50-5. Chemistry - A European Journal 59. Manabe, K.; Kobayashi, S. Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions in Aqueous Media. 2002, 8(18), 4094-101. 60. Hafez, A. M.; Taggi, A. E.; Lectka, T. Sequential Column Asymmetric Catalysis. 2002, 8(18), 4114-9. 61. Pohl, M.; Lingen, B.; Muller, M. Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation. 2002, 8(23), 5288-95. Chemistry of Heterocyclic Compounds 62. Abramov, A. A.; Anisimov, A. V.; Bobyleva, A. A. Synthesis of Oxathiacrown Compounds by the Reactions of Sulfur Dichloride with Unsaturated Compounds and Their Extraction Characteristics. 2002, 38(3), 261-73. 63. Donskaya, O. V.; Dolgushin, G. V.; Lopyrev, V. A. Vicarious Nucleophilic Substitution of Hydrogen in NitroSubstituted Pyrroles, Azoles, and Benzannelated Systems Based on Them. 2002, 38(4), 371-84. 64. Mashkina, A. V. Catalytic Synthesis of Some Sulfur-Containing Heterocyclic Compounds. (Review). 2002, 38(5), 503-23. 65. Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. Molecular Structure of Thiophene 1,1-Dioxides, Thiophene S-Oxides, and Their Derivatives. 2002, 38(6), 632-645. 66. Sliwa, W.; Deska, M. Cavitands. 2002, 38(6), 64667. 67. Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. Molecular Structure of Selenophenes and Tellurophenes. 2002, 38(7), 763-77. 68. Khilya, V. P.; Ishchenko, V. V. Flavones, Isoflavones, and 2- and 3-Hetarylchromones in Reactions with Hydroxylamine. (Review). 2002, 38(8), 883-99. CHEMTRACTS: Organic Chemistry 69. Seganish, W. M.; Jarvis, B. B. Design and Synthesis of Pyrrolidine-5,5-Trans-Lactams as Novel Mechanism Based Inhibitors of Human Cytomegalovirus Protease. 2002, 15(7), 367-72. 70. Brummond, K. M. Synthesis of (()-Arisugacin A Using a Formal [3+3] Cycloaddition Reaction. 2002, 15(7), 373-9. 71. Cauble, D. F., Jr.; Krische, M. J. The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes. 2002, 15(7), 380-3. 72. Sheehan, S. M. Proline-Catalyzed Asymmetric Mannich Reactions: The Highly Enantioselective Synthesis of Amino Acid Derivatives and 1,2-Amino Alcohols. 2002, 15(7), 384-90. 73. Bianchini, C.; Giambastiani, G. On the Origin of Opposite Stereoselection in the Asymmetric Hydrogenation of Phenyl- and Tert-Butyl-Substituted Enamides: Asymmetric Hydrogenation of Enamides with Rh-Bisp and Rh-Miniphos Catalysts: Scope, Limitations, and Mechanism. 2002, 15(8), 430-7. 74. Bianchini, C.; Giambastiani, G.; Valacchi, M. Palladium-Catalyzed Arylation of Malonates and Cya-

noesters Using Sterically Hindered Trialkyl- and Ferrocenyldialkylphosphine Ligands. A General and Mild Copper-Catalyzed Arylation of Diethyl Malonate. 2002, 15(8), 438-43. 75. Archer, E. A.; Krische, M. J. Second Generation Light-Driven Molecular Motors: Unidirectional Rotation Controlled by a Single Stereogenic Center with NearPerfect Photoequilibria and Acceleration of the Speed of Rotation by Structural Modification. 2002, 15(9), 46574. 76. Watson, J. A., Jr.; Jarvis, B. B. Total Synthesis of Nominal Diazonamides. Part 1: Convergent Preparation of the Structure Proposed for (-)-Diazonamide A. Part 2: On the True Structure and Origin of Natural Isolates. 2002, 15(9), 481-6. 77. Cossy, J.; Gomez Pardo, D. Synthesis of Substituted Piperidines via Aziridinium Intermediates: Synthetic Applications. 2002, 15(11), 579-605. 78. Uffman, E. W.; Gilbertson, S. R. A Novel PeptideBased Encoding System for “One-Bead One-Compound” Peptidomimetic and Small Molecule Combinatorial Libraries. 2002, 15(11), 606-10. 79. Leach, A. G.; Houk, K. N. An Unexpected Bispericyclic Transition Structure Leading to 4 + 2 and 2 + 4 Cycloadducts in the Endo Dimerization of Cyclopentadiene. 2002, 15(11), 611-6. 80. Paul, N. M.; Gabriel, C. J.; Parquette, J. R. Developments in Fluorous Mitsunobu Chemistry. 2002, 15(11), 617-22. 81. Preston, A. J.; Hofacker, A. L.; Parquette, J. R. Rhodium Catalyzed Ortho-Alkylation of Aromatic Aldimines and Ketimines with Olefins via C-H Bond Activation. 2002, 15(11), 623-9. 82. Harned, A. M.; Hanson, P. R.; Flynn, D. L. Natural Product Synthesis Utilizing Solid-Supported Reagents. 2002, 15(11), 630-6. Chirality 83. Nishide, K.; Node, M. Recent Development of Asymmetric Syntheses Based on the Meerwein-PonndorfVerley Reduction. 2002, 14(10), 759-67. Coordination Chemistry Reviews 84. Valliant, J. F.; Guenther, K. J.; King, A. S.; Morel, P.; Schaffer, P.; Sogbein, O. O.; Stephenson, K. A. The Medicinal Chemistry of Carboranes. 2002, 232(1-2), 173-230. 85. Bunten, K. A.; Chen, L.; Fernandez, A. L.; Poe, A. J. Cone Angles: Tolman’s and Plato’s. 2002, 233-4, 4151. 86. Brydges, S.; Harrington, L. E.; McGlinchey, M. J. Sterically Hindered Organometallics: Multi-n-Rotor (n ) 5, 6 and 7) Molecular Propellers and the Search for Correlated Rotations. 2002, 233-4, 75-105. 87. Hoskin, A. J.; Stephan, D. W. Early Transition Metal Hydride Complexes: Synthesis and Reactivity. 2002, 233-4, 107-29. 88. Piers, W. E.; Emslie, D. J. H. Non-Cyclopentadienyl Ancillaries in Organogroup 3 Metal Chemistry: A Fine Balance in Ligand Design. 2002, 233-4, 131-55. J. Org. Chem, Vol. 68, No. 14, 2003 5797

89. Zargarian, D. Group 10 Metal Indenyl Complexes. 2002, 233-4, 157-76. 90. Harvey, P. D. Wide-Rim and Outer-Face Functionalizations of Calix[4]arene. 2002, 233-4, 289-309. 91. Chandrasekhar, V.; Nagendran, S.; Baskar, V. Organotin Assemblies Containing Sn-O Bonds. 2002, 235(1-2), 1-52. 92. Hoefelmeyer, J. D.; Schulte, M.; Tschinkl, M.; Gabbai, F. P. Naphthalene Derivatives Peri-Substituted by Group 13 Elements. 2002, 235(1-2), 93-103.

109. Wijnberg, J. B. P. A.; De Groot, A. Induced Ionization in 1,4-Diol Monosulfonate Esters and its Application in the Synthesis of Natural Products. 2003, 7(3), 257-74. 110. Sotomayor, N.; Lete, E. Aryl and Heteroaryllithium Compounds by Metal-Halogen Exchange. Synthesis of Carbocyclic and Heterocyclic Systems. 2003, 7(3), 275-300. 111. Pena, P. C. A.; Roberts, S. M. The Chemistry of Epoxy Alcohols. 2003, 7(6), 555-71.

Current Organic Chemistry

Heterocycles

93. Kotali, A. Reactions of Hydrazones with Lead Tetraacetate in Organic Synthesis. 2002, 6(11), 965-85. 94. Trofimov, B. A. Acetylene and its Derivatives in Reactions with Nucleophiles: Recent Advances and Current Trends. 2002, 6(13), 1121-62. 95. Kondo, T.; Mitsudo, T.-A. Advances in Ruthenium Catalysis. Novel Catalytic Reactions via η3-Allylruthenium Intermediates. 2002, 6(13), 1163-79. 96. Schobert, R.; Gordon, G. J. Bioactive Heterocycles from Domino Wittig-Pericyclic Reactions. 2002, 6(13), 1181-96. 97. Rahman, N. A.; Landais, Y. Desymmetrisation of Cyclic Dienes. An Efficient Strategy for Natural Products Synthesis. 2002, 6(15), 1369-95. 98. Dugave, C. Study of the Cis-Trans Isomerization of the Amino-Acyl Prolyl Peptide Bond. Application to the Design of Novel Inhibitors of Immunophilins. 2002, 6(15), 1397-431. 99. Moreno, I.; Tellitu, I.; Herrero, M. T.; SanMartin, R.; Dominguez, E. New Perspectives for Iodine (III) Reagents in (Hetero)Biaryl Coupling Reactions. 2002, 6(15), 1433-52. 100. Engel, R.; Cohen, J. I. Organic Polycationic Saltss Syntheses and Applications. 2002, 6(15), 1453-67. 101. Murafuji, T.; Kurotobi, K.; Nakamura, N.; Sugihara, Y. Recent Advances in the Synthesis of Optically Active Compounds Bearing a Chiral Heteroatom Center in the Group 13-16 Elements. 2002, 6(15), 1469-94. 102. Jarosz, S.; Zamojski, A. Carbohydrate Derivatives Containing the Carbon-Lithium and Carbon-Tin Bonds. 2003, 7(1), 13-33. 103. Demchenko, A. V. 1,2-cis O-Glycosylation: Methods, Strategies, Principles. 2003, 7(1), 35-79. 104. Kuroda, C.; Suzuki, H. Synthesis of Odd-Membered Rings by the Reaction of β- Carbonylallylsilane or its Derivative as a Carbon 1,3-Dipole. 2003, 7(2), 11531. 105. Kobayashi, Y. Installation of Carbon Nucleophiles onto Monoacetate of 4-Cyclopentene-1,3-Diol and Synthesis of Cyclopentanoids. 2003, 7(2), 133-47. 106. Avendano, C.; Menendez, J. C. Chemistry of Pyrazino[2,1-b]quinazoline-3,6-diones. 2003, 7(2), 14973. 107. Koketsu, M.; Ishihara, H. Synthesis of 1,3Selenazine and 1,3-Selenazole and Their Biological Activities. 2003, 7(2), 175-85. 108. Mead, K. T.; Brewer, B. N. Strategies in Spiroketal Synthesis Revisited: Recent Applications and Advances. 2003, 7(3), 227-56.

112. Sliwa, W.; Matusiak, G.; Deska, M. Cavitands and Related Container Molecules. 2002, 57(11), 2179-206. 113. Majumdar, K. C.; Basu, P. K. Formation of Fiveand Six-Membered Heterocyclic Rings by Radical Cyclization. 2002, 57(12), 2413-39. 114. Cacchi, S.; Fabrizi, G.; Parisi, L. M. NitrogenContaining Heterocycles via Palladium-Catalyzed Reaction of Alkynes with Organic Halides or Triflates. 2002, 58, 667-82. 115. Sakamoto, M.; Nishio, T. Photochemistry of Nitrogen-Containing Thiocarbonyl Compounds. 2003, 59(1), 399-427. 116. Sato, T.; Ikeda, M. A General Route to Bridged Azabicyclic Compounds Using Radical Translocation/ Cyclization Reactions. 2003, 59(1), 429-40.

5798 J. Org. Chem., Vol. 68, No. 14, 2003

Journal of Fluorine Chemistry 117. Pashinnik, V. E. Advances in the Chemistry of Organylfluorosulfurans at the Institute of Organic Chemistry, Kiev, Ukraine. 2002, 117(2), 85-98. Journal of the Transactions 1

Chemical

Society,

Perkin

118. Collins, I. Rapid Analogue Syntheses of Heteroaromatic Compounds. 2002, (17), 1921-40. 119. van Steenis, J. H.; van der Gen, A. Synthesis of Terminal Monofluoro Olefins. 2002, (19), 2117-33. 120. King, A. S. H.; Twyman, L. J. Heterogeneous and Solid Supported Dendrimer Catalysts. 2002, (20), 220918. 121. Jensen, K. J. O-Glycosylations Under Neutral or Basic Conditions. 2002, (20), 2219-33. 122. Elliott, M. C. Saturated Oxygen Heterocycles. 2002, (21), 2301-23. 123. Carter, N. B.; Nadany, A. E.; Sweeney, J. B. Recent Developments in the Synthesis of Furan-2(5H)ones. 2002, (21), 2324-42. 124. Osborn, H. M. I.; Gemmell, N.; Harwood, L. M. 1,3-Dipolar Cycloaddition Reactions of Carbohydrate Derived Nitrones and Oximes. 2002, (22), 2419-38. 125. Blakemore, P. R. The Modified Julia Olefination: Alkene Synthesis via the Condensation of Metallated Heteroarylalkylsulfones with Carbonyl Compounds. 2002, (23), 2563-85. 126. Adams, J. P. Nitro and Related Groups. 2002, (23), 2586-97. 127. Bodkin, J. A.; McLeod, M. D. The Sharpless Asymmetric Aminohydroxylation. 2002, (24), 2733-46.

128. Bowman, W. R.; Fletcher, A. J.; Potts, G. B. S. Synthesis of Heterocycles by Radical Cyclisation. 2002, (24), 2747-62. 129. Hartley, R. C.; McKiernan, G. J. Titanium Reagents for the Alkylidenation of Carboxylic Acid and Carbonic Acid Derivatives. 2002, (24), 2763-93. Natural Product Reports 130. Moloney, M. G. Excitatory Amino Acids. 2002, 19(5), 597-616. 131. Michael, J. P. Indolizidine and Quinolizidine Alkaloids. 2002, 19(6), 719-41. 132. Michael, J. P. Quinoline, Quinazoline and Acridone Alkaloids. 2002, 19(6), 742-60. 133. Liddell, J. R. Pyrrolizidine Alkaloids. 2002, 19(6), 773-81. Organic Preparations International

and

Procedures

134. Blanchet, J.; Bonin, M.; Micouin, L. Recent Progress in the Asymmetric Synthesis of R-Substituted Propargylamines. 2002, 34(5), 457-82. 135. Kinder, F. R., Jr. Synthetic Approaches Toward the Bengamide Family of Antitumor Marine Natural Products. A Review. 2002, 34(6), 559,561-83. 136. Cheng, W.-C.; Kurth, M. J. The Zincke Reaction. A Review. 2002, 34(6), 585,587-608. 137. Pellissier, H.; Santelli, M. The Birch Reduction of Steroids. A Review. 2002, 34(6), 609,611-42. Photochemistry 138. Gilbert, A. Photochemistry. Introduction and Review of the Year. 2002, 33, 1-10. 139. Harriman, A. Photophysical Processes in Condensed Phases. 2002, 33, 13-49. 140. Horspool, W. M. Photolysis of Carbonyl Compounds. 2002, 33, 53-73. 141. Horspool, W. M. Enone Cycloadditions and Rearrangements: Photoreactions of Dienones and Quinones. 2002, 33, 74-118. 142. Horspool, W. M. Photochemistry of Alkenes, Alkynes and Related Compounds. 2002, 33, 119-54. 143. Gilbert, A. Photochemistry of Aromatic Compounds. 2002, 33, 155-93. 144. Cox, A. Photo-Reduction and -Oxidation. 2002, 33, 194-241. 145. Pratt, A. C. Photoreactions of Compounds Containing Heteroatoms other than Oxygen. 2002, 33, 242306. 146. Dunkin, I. R. Photoelimination. 2002, 33, 30736. Pure and Applied Chemistry 147. Barluenga, J. Fischer Carbene Complexes. A New Tool for Heterocyclic Synthesis. 2002, 74(8), 1317-25.

148. Beletskaya, I. P. Transition Metal-Catalyzed Reactions in Heterocyclic Chemistry. 2002, 74(8), 132737. Russian Chemical Reviews 149. Kizhnyaev, V. N.; Vereshchagin, L. I. Vinyltetrazoles: Synthesis and Properties. 2003, 72(2), 143-64. 150. Kiryuhin, D. P.; Barkalov, I. M. Chain Chemical Reactions at Low Temperatures. 2003, 72(3), 217-31. 151. Shastin, A. V.; Godovikova, T. I.; Korsunskii, B. L. Nitro Derivatives of 1,3,5-Triazine: Synthesis and Properties. 2003, 72(3), 279-87. Russian Journal of Organic Chemistry 152. Furin, G. G. Internal Perfluoroolefins in the Synthesis of Organofluorine Compounds. 2002, 38(7), 921-61. 153. Kofman, T. P. 5-Amino-3-nitro-1,2,4-triazole and its Derivatives. 2002, 38(9), 1231-43. 154. Beletskaya, I. P.; Kazankova, M. A. Catalytic Methods for Building up Phosphorus-Carbon Bond. 2002, 38(10), 1391-430. Science 155. Marko, I. E.; Sterin, S.; Buisine, O.; Mignani, G.; Branlard, P.; Tinant, B.; Declercq, J.-P. Selective and Efficient Platinum(0)-Carbene Complexes as Hydrosilylation Catalysts. 2002, 298(5591), 204-7. 156. Steed, J. W. Molecular “Ghosts”. 2002, 298(5595), 976-7. 157. Atwood, J. L.; Barbour, L. J.; Jerga, A.; Schottel, B. L. Guest Transport in a Nonporous Organic Solid via Dynamic van der Waals Cooperativity. 2002, 298(5595), 1000-2. 158. Movassaghi, M.; Jacobsen, E. N. Perspectives: Chemistry: The Simplest “Enzyme”. 2002, 298(5600), 1904-5. 159. McMahon, R. J. Chemistry: Chemical Reactions Involving Quantum Tunneling. 2003, 299(5608), 8334. 160. Zuev, P. S.; Sheridan, R. S.; Albu, T. V.; Truhlar, D. G.; Hrovat, D. A.; Borden, W. T. Carbon Tunneling from a Single Quantum State. 2003, 299(5608), 867-70. Synlett 161. Metallinos, C. The N-Cumyl Group for Facile Manipulation of Carboxamides, Sulfonamides and Aryl O-Carbamates. Post-Directed Ortho Metalation. 2002, (9), 1556-7. 162. Mikami, K.; Aikawa, K.; Yusa, Y.; Jodry, J. J.; Yamanaka, M. Tropos or Atropos? That is the Question! 2002, (10), 1561-78. 163. Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Advances and Adventures in Amination Reactions of Olefins and Alkynes. 2002, (10), 1579-94. 164. Cossy, J.; BouzBouz, S.; Pradaux, F.; Willis, C.; Bellosta, V. Chiral Titanium Complexes. Synthesis of Optically Active Unsaturated Alcohols, Diols, PolyproJ. Org. Chem, Vol. 68, No. 14, 2003 5799

pionates and Their use in the Synthesis of Biologically Active Compounds. 2002, (10), 1595-606. 165. Raehm, L.; Hamilton, D. G.; Sanders, J. K. M. From Kinetic to Thermodynamic Assembly of Catenanes: Error Checking, Supramolecular Protection and Oligocatenanes. 2002, (11), 1743-61. 166. Prabhu, K. R.; Devan, N.; Chandrasekaran, S. Chemistry of Tetrathiomolybdate: Applications in Organic Synthesis. 2002, (11), 1762-78. 167. Tykwinski, R. R.; Zhao, Y. Cross-Conjugated Oligo(enynes). 2002, (12), 1939-53. 168. Takeuchi, R. Iridium Complex-Catalyzed Highly Selective Organic Synthesis. 2002, (12), 1954-65. 169. Togo, H.; Sakuratani, K. Polymer-Supported Hypervalent Iodine Reagents. 2002, (12), 1966-75. 170. Corsi, M. Jacobson’s Catalyst. 2002, (12), 21278. 171. Biali, S. E. The Spirodienone Route for the Functionalization of Calixarenes. 2003, (1), 1-11. 172. Huddleston, R. R.; Krische, M. J. Enones as Latent Enolates in Catalytic Processes: Catalytic Cycloreduction, Cycloaddition and Cycloisomerization. 2003, (1), 12-21. 173. Hoarau, C.; Pettus, T. R. R. Strategies for the Preparation of Differentially Protected Ortho-Prenylated Phenols. 2003, (1), 127-37. 174. Tasneem Vilsmeier-Haack Reagent (Halomethyleneiminium Salt). 2003, (1), 138-9. 175. Minatti, A. Iodosobenzene (PhIO). 2003, (1), 1401. SynthesissStuttgart 176. Saljoughian, M. Synthetic Tritium Labeling: Reagents and Methodologies. 2002, (13), 1781-801. 177. Chambert, S.; Desire, J.; Decout, J.-L. The 2-(Trimethylsilyl)ethyl Sulfur Group in Synthesis. 2002, (16), 2319-34. 178. Chinkov, N.; Chechik, H.; Majumdar, S.; Liard, A.; Marek, I. New Preparation of sp2 Organometallic Derivatives. 2002, (17), 2473-83. 179. Singh, R. P.; Shreeve, J. M. Recent Advances in Nucleophilic Fluorination Reactions of Organic Compounds Using Deoxofluor and DAST. 2002, (17), 256178.

180. Ramig, K. Synthesis and Reactions of Fluoroether Anesthetics. 2002, (17), 2627-31. 181. Molt, O.; Schrader, T. Asymmetric Synthesis with Chiral Cyclic Phosphorus Auxiliaries. 2002, (18), 263370. 182. Poulsen, C. S.; Madsen, R. Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes. 2003, (1), 1-18. Tetrahedron 183. Liu, M.; Sibi, M. P. Recent Advances in the Stereoselective Synthesis of β-Amino Acids. 2002, 58(40), 7991-8035. 184. Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Applications of Bismuth(III) Compounds in Organic Synthesis. 2002, 58(42), 8373-97. 185. Park, K.-H.; Kurth, M. J. Cyclic Amino Acid Derivatives. 2002, 58(43), 8629-59. 186. Reese, C. B. The Chemical Synthesis of Oligo- and Poly-Nucleotides: A Personal Commentary. 2002, 58(44), 8893-920. 187. Silva, L. F. Construction of Cyclopentyl Units by Ring Contraction Reactions. 2002, 58(45), 9137-61. 188. Blass, B. E. KF/Al2O3 Mediated Organic Synthesis. 2002, 58(46), 9301-20. 189. Armstrong, A.; Blench, T. J. Recent Synthetic Studies on the Zaragozic Acids (Squalestatins). 2002, 58(46), 9321-49. 190. Marek, I. Sp3 Organozinc Carbenoid Homologation in Organic Synthesis. 2002, 58(47), 9463-75. 191. Mehta, G.; Muthusamy, S. Tandem CyclizationCycloaddition Reactions of Rhodium Generated Carbenoids from R-Diazo Carbonyl Compounds. 2002, 58(47), 9477-504. 192. Kotha, S.; Lahiri, K.; Kashinath, D. Recent Applications of the Suzuki-Miyaura Cross-Coupling Reaction in Organic Synthesis. 2002, 58(48), 9633-95. 193. de Koning, C. B.; Rousseau, A. L.; van Otterlo, W. A. L. Modern Methods for the Synthesis of Substituted Naphthalenes. 2002, Volume Date 2003, 59(1), 7-36.

Contributed Volumes Amino Acids, Peptides and Proteins. Volume 33. Barrett, G. C., Davies, J. S., Eds., Royal Society of Chemistry: Cambridge, U.K., 2002. 194. Chang, W. C.; Higton, A. Amino Acids. 195. Elmore, D. Peptide Synthesis. 196. Davies, J. S. Analogue and Conformational Studies on Peptides, Hormones and Other Biologically Active Peptides. 197. Davies, J. S. Cyclic, Modified and Conjugated Peptides. 198. Farkas, E.; Sovago, I. Metal Complexes of Amino Acids and Peptides. 199. Barrett, G. C. Proteins. 5800 J. Org. Chem., Vol. 68, No. 14, 2003

Organic Synthesis Theory and Applications, Volume 5. Hudlicky, T., Ed., Elsevier Science: Oxford, U.K., 2001. 200. Hansen, T. V.; Stenstrøm, Y. Naturally Occurring Cyclobutanes. 201. Brocksom, T. J.; Brocksom, U. et al. Diels-Alder Reactions in the Synthesis of Higher Terpenes. 202. Natchus, M. G.; Tian, X. The Asymmetric Synthesis of Unnatural Amino Acids as Building Blocks for Complex Molecular Synthesis. 203. Wright, D. L. et al. The Role of Organic Synthesis in the Generation of Molecular Diversity.

Monographs 204. Atta ur, R., Ed. Bioactive Natural Products, Part H. [In: Stud. Nat. Prod. Chem., 2002; 27]. Elsevier Science: Amsterdam, Netherlands, 2002. 205. Chu, C. K. Recent Advances in Nucleosides: Chemistry and Chemotherapy. Elsevier Science: Amsterdam, Netherlands, 2002. 206. Gilbert, A. Photochemistry. Introduction and Review of the Year. Royal Society of Chemistry: Cambridge, U.K., 2002. 207. Hanson, J. R. Tutorial Chemistry Texts, 12; Organic Synthetic Methods. Royal Society of Chemistry: Cambridge, U.K., 2002. 208. Hepworth, J. D.; Waring, D. R.; Waring, M. J. Tutorial Chemistry Texts, Volume 13; Aromatic Chemistry. Royal Society of Chemistry: Cambridge, U.K., 2002. 209. Herrmann, W. A., Werner, H., Eds. Selective Reactions of Metal-Activated Molecules. [In: J. Organomet. Chem., 2002; 661(1-2)]. Elsevier Science: Amsterdam, Netherlands, 2002. 210. Kadish, K. M., Smith, K. M., Guilard, R., Eds. The Porphyrin Handbook. Academic Press: San Diego, CA, 2000. 211. Kurosawa, H.; Yamamoto, A. Fundamentals of Molecular Catalysis. Elsevier: San Diego, CA, 2003. 212. Loakes, D., Ed. Modified Nucleosides Synthesis and Applications. Research Singpost: Trivandrum, India, 2002. 213. Maas, G., Ed. Science of Synthesis, Volume 9, Houben-Weyl Methods of Molecular Transformations; Hetarenes and Related Ring Systems: Fully Unsaturated Small-Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom. Georg Thieme Verlag: Stuttgart, Germany, 2002. 214. Martin, R. Handbook of Hydroxybenzophenones. Kluwer Academic: Dordrecht, Netherlands, 2000.

215. Nakamura, T., Matsumoto, T., Tada, H., Sugiura, K. I., Eds. Chemistry of Nanomolecular Systems: Towards the Realization of Molecular Devices. [In: Springer Ser. Chem. Phys., 2003; 70]. Springer-Verlag: Berlin, Germany, 2003. 216. Negishi, E.-i., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis, Volume 1. John Wiley & Sons: Hoboken, NJ, 2002. 217. Osborn, H. M. I.; Harwood, L. M. Best Synthetic Methods: Carbohydrates. Academic Press: San Diego, CA, 2003. 218. Pyatnitsky, Y. I.; Pavlenko, M. V.; Ilchenko, N. I. Introduction to Non-Linear Kinetics in Heterogeneous Catalysis. Nova Sci Publishers: Huntington, NY, 2000. 219. Schaumann, E., Ed. Houben-Weyl Methods of Molecular Transformations: Hetarenes and Related Ring Systems. (Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom.) [In: Sci. Synth., 2002; 11]. Georg Thieme Verlag: Stuttgart, Germany, 2002. 220. Schweizer, F. M., Ed. Combinatorial Carbohydrates. [In: Comb. Chem. High Throughput Screening, 2002; 5(5)]. Bentham Science Publishers: Hilversum, Netherlands, 2002. 221. Shuttleworth, S. J., Ed. Development and Applications of Polymer-Supported Reagents and Ion Exchange Resins in Organic Synthesis and Combinatorial Chemistry. [In: Comb. Chem. High Throughput Screening, 2002; 5(3)] Bentham Science Publishers: Hilversum, Netherlands, 2002. 222. Taylor, P., Ed. The Molecular World: Mechanism and Synthesis. Royal Society of Chemistry: Cambridge, U.K., 2002. 223. Taylor, P., Gagan, M., Eds. The Molecular World: Alkenes and Aromatics. Royal Society of Chemistry: Cambridge, U.K., 2002.

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Index Acetylene, ethynylation, 94 reaction with nucleophiles, 94 vinylation, 94 Acetylenylpyrazoles, 11 Acridone alkaloids, 132 Aldehydes, aromatic, alkylated, preparation, 81 enantioselective cross aldol condensation, 71 from allylic alcohols, 33 preparation, stereoselective hydroformylation, 4 reductive amination, 9 Aldimines, aromatic, ortho-alkylation, 81 Aldol condensation, lanthanide catalyst, 17 Alkaloids, pyrrolizidine, 133 Alkanes, cryochemical polymerisation, 150 Alkenes, book, 223 cryochemical polymerization, 150 hydrovinylation, 18 metathesis, with catenanes, 165 Sharpless stereoselective aminohydroxylation, 10 synthesis, via Julia olefination, 125 Alkynes, amination, 163 reaction with organic halides, 114 reaction with organic triflates, 114 Allene ethers, cationic cyclopentannelation, 5 Allenes, from cyclopropanes, 45 Allylic alcohols, transposition, 33 Allylic alkylation, Ir catalyst, 168 Allylruthenium intermediates, 95 Allyltitanium complex, 164 Alumina, in organic reaction, 188 Amide carbamates, metalation, 161 Amines, preparation, 9 preparation, base catalysts, 7 Amino acids, β-, asymmetric synthesis, 183 book, 194, 198 cyclic, constrained, 185 dialkylated, 6 excitatory, 130 glycosyl, book, 217 synthesis, ring closing metathesis, 6 unnatural, in synthesis, book, 202 Aminohydroxylation, Sharpless, asymmetric, 127 Anti AIDS agent, 98 Antitumor agents, bengamides, 135 Arisugacin, synthesis via cycloaddition, 70 Aromatics, book, 223 tutorials, book, 208 Aryl chlorides, Pd catalyzed coupling, 21 Arylation, regioselective, 2 Aryllithium, metal halogen exchange, 110 Asymmetric aldol addition, proline catalyst, 158 Asymmetric catalysis, atropos ligand, 162 lanthanide catalyst, 17 tropos ligand, 162

Asymmetric synthesis, phosphorus ligands, 53 phosphorus auxiliary, chiral, cyclic, 181 Aziridines, 52 Azoles, H nucleophilic substitution, 63 Baylis Hillman reaction, 39 Sharpless aminohydroxylation, 10 Bengamides, antitumor agents, 135 Benzannelated compounds, 63 Benzodiazepines, combinatorial synthesis, 40 Benzophenones, hydroxy, book, 214 Biaryl coupling, iodine reagent, 99 Bismuth compounds, in organic synthesis, 184 Bond dissociation energies, 3 Boron neutron capture therapy agent, carboranes, 84 Cage compounds, 58 self-assembled, 30 Calixarenes, functionalization, 171 functionalized rim, 90 in vinyl bromide, molecular diffusion, 156-7 Carbamate, ortho metalation, 161 Carbenoids, tandem cyclization-cycloaddition, 191 from R-diazo carbonyl compounds, 191 Carbocations, thermodynamic stability, 14 Carbocycles, eight membered, Fischer carbenes, 147 Carbohydrate donors, book, 217 Carbohydrates, 1,3-dipolar cycloaddition, 124 with C-Li bonds, 102 with C-Sn bonds, 102 with sialic acid, book, 217 Carbon 1,3-dipoles, 104 Carbon tunneling, 159-60 Carbonic acid, alkylidenation, Ti reagent, 129 Carbonyl ylide formation, Rh catalyst, 191 Carbonylallylsilane synthons, 104 Carboranes, medicinal chemistry, 84 Carboxamides, ortho metalation, 161 Carboxylic acid alkylidenation, Ti reagent, 129 Catalysis, book, 211 heterogeneous, non-linear kinetics, 218 homogeneous and heterogeneous, 28 surface organometallic chemistry, 28 Catananes, alkene metathesis, 165 Mitsunobu alkylation, 165 self-assembly, 165 supramolecular template, 165 Cavitands, 66, 112 C-C bond formation, aqueous media, 59 silicon Lewis acid, 37 thiamine diphosphate dependent enzyme, 61 Central nervous system agents, 130 C-H bond activation, 1

5802 J. Org. Chem., Vol. 68, No. 14, 2003

Chain compounds, transition metal backbone, 23 Chromones, hetaryl-, with hydroxylamine, 68 Combinatorial chemistry, amino acids, 6 book, 203, 221 carbohydrates, 220 parallel kinetic resolution, 56 separation techniques, 19 Combinatorial synthesis, indoles, 40 benzimidazoles, 40 benzodiazepines, 40 piperazines, 40 pyridines, 40 pyrimidines, 40 Crotyltitanium complex, 164 Cumyl group, regioselective metalation, 161 Cyanoesters, arylation, 74 Cycloaddition, with Fischer carbenes, 147 Cyclobutanes, natural, 200 Cyclohexadienes, Sharpless stereoselective aminohydroxylation, 10 Cyclopentadiene dimerization, pericyclic transition state, 79 Cyclopentadienyl transition metal complexes, 89 Cyclopentenediol acetate, 105 Cyclopentenes, from vinylcyclopropanes, 47 Cyclopentenoids, preparation, 105 Cyclopentenone, catalytic preparation, 95 Cyclopentyl unit formation, ring contraction, 187 Cyclophanes, polyunsaturated, 20 Cyclopropanes, donor acceptor substituted, 46 fluorinated, 43 photoelectron spectra, 41 Cycloproparenes, 50 Cyclopropene-carbene rearrangement, 48 Cyclopropenes, fluorinated, 43 Ge-, Si-, Sn-, 51 photoelectron spectra, 41 Cyclopropenone acetals, 49 Cyclopropylallenes ring expansion, 45 Heck reaction, 45 Myers Saito cyclization, 45 Cytomegalovirus protease inhibitors, 69 Dendrimer catalysts, solid supported, 120 Diazo compounds, preparation, 93 Diazonamide A, total synthesis, 76 Diels-Alder reaction, lanthanide catalyst, 17 Dienes, cyclic, desymmetrization, 97 Diethyl malonate, arylation, 74 Dihydrothiophene oxides, 65 Diisopropylethylamine hydrofluoride reagent, 180 Diols, unsaturated, 164 Electron transfer, nucleophilic substitution, 34 Enamides, substituted, asymmetric hydrogenation, 73 Enones, catalytic reactions, 172 cycloaddition, 141

Enyne metathesis, Ru carbene complex, 182 Enyne oligomers, cross conjugated, 167 Epoxy alcohols, 111 Esters, monosulfonate diols, ionization, 109 Fischer carbene complex, heterocyclic synthesis, 147 kinetics and thermodynamics, 15 Flavones, with hydroxylamines, 68 Fluorination, nucleophilic, with DAST, 179 nucleophilic, with deoxofluor, 179 Fluoroalkoxyfluoro sulfuranes, preparation, 117 Fluoroether anesthetics, 180 Fluorous Mitsunobu reactions, 80 Furanones, preparation, 123 Gelsemine, asymmetric preparation, 26 Glycosidation, book, 217 Glycosides, aliphatic, preparation, 121 C-linked, book, 217 Glycosylation, ortho-, 121 stereoselective, 1,2-cis, 103 Group IIIA IVA chiral compounds, 101 Group VA VIA chiral compounds, 101 Grubbs reagent, for alkylidenation, 129 Guest transport, nonporous organic solid, 156-7 Halocyclopropanes, dehalogenation, 45 phase transfer synthesis, 44 reductive dehalogenation, 44 Hetarenes, Houben Weyl transformation, book, 213, 219 preparation, book, 213 Heteroaromatics, arylation, 118 coupling, 118 cycloaddition, 118 rapid analog synthesis, 118 substitution, 118 Heteroarylalkylsulfones, metallated, condensation with carbonyls, 125 Heteroaryllithium, metal halogen exchange, 110 Heterobiaryl coupling, iodine reagent, 99 Heterocycles, azabicyclic, preparation, 116 bioactive, via domino Wittig pericyclic reaction, 96 five, six membered ring, 113 from heteroaryllithium, 110 from thioamide synthons, 36 nitrogen-, preparation, 114 oxygen-, preparation, 122 preparation, from acetylene, 94 preparation, radical cyclization, 128 sulfur-, preparation, 64 synthesis, with Fischer carbenes, 147 via radical cyclization, 113 Heterogeneous catalysts, solid support dendrimers, 120 Heteroporphyrins, book, 210 Hormones, book, 196 Hydrazones, with lead tetraacetate, 93 Hydroformylation, stereoselective, 4 Hydrogen transfer reduction, catalyst, 8 Hydrogenation, lanthanide catalyst, 17 polymer supported catalyst, 8 Hydrosilation, platinum-carbene complexes, 155 Hydrovinylation catalyst, 18

Hydroxyindoles, 12 Hydroxytryptamines, 12 Hydroxytryptophans, 12 Immunophilin inhibitors, 98 Indazole preparation, 93 Indenyl transition metal complexes, 89 Indoles, combinatorial synthesis, 40 Indolizidine alkaloids, 131 Iodine, hypervalent, oxidation reagent, 169 Iodosobenzene, 175 Iridium complex catalyst, 168 Isoflavones, with hydroxylamines, 68 Isopolydiacetylene oligomer, 167 Isopolytriacetylene oligome, 167 Isoxazolidines, synthesis, 124 Isoxazolines, synthesis, 124 Jacobson epoxidation catalyst, 170 Julia olefination, modified, 125 Ketimines, aromatic, ortho-alkylation, 81 Ketones, aromatic, alkylated, preparation, 81 from allylic alcohols, 33 reductive amination, 9 Kinetic resolution, chiral compounds, 56 Lactides, polymerisation, 88 Lewis acids, silicon, C-C bond formation, 37 Ligands, P-donor, 53 Lupin alkaloids, 131 Macrolides, marine, 24 Magnetic fields, in radical reactions, 54 Malonates, arylation, 74 Mannosides, synthesis, book, 217 Meerwein Ponndorf Verley reduction, 83 Metacyclophanes, 90 Metal activated molecules, 209 Metallaboranes, 22 Metallocenes, early transition metal hydride complex, 87 Methylcyclobutylfluorocarbene ring expansion matrix, 160 Michael Addition, lanthanide catalyst, 17 Mitsunobu reaction, fluorous, 80 Molecular devices, 215 Molecular motors, light-driven, 75 Monofluoro-olefins, preparation, 119 Nanomolecules, 215 Nanospaces, self-assembled, 30 Naphthalenes, perisubstituted, group 13, 92 substituted, preparation, 193 Natural product synthesis, from cyclic dienes, 97 solid supported reagents, 82 using diol monosulfonate esters, 109 Natural products, bioactive, book, 204 cyclopentyl unit, 187 marine, bengamides, 135 N-containing, 126 -oligocyclopropyl, 42 Necic acid, 133 Nickel catalyst, heterocyclic substitution, 148 Nitrile oxide group, in reactions, 126 Nitriles, arylation, 2 hydrogenation, 9 Nitro group, compounds, in reactions, 126

Nitroalkyltriazines, 151 Nitroaminotriazines, 151 Nitroso group, in reactions, 126 Nitrotriazines, 151 Nitrotriazolamines, 153 Nucleophilic substitution, electron transfer, 34 Nucleosides, chemotherapy, book, 205 derivatives, book, 212 Olefins, amination, 88, 163 hydroamination, green synthesis, 7 hydrogenation, 88 hydrosilation, 88 metathesis, book, 211 polymerization, 88 polysubstituted, metalated, 178 terminal monofluoro, preparation, 119 Oligocatenanes, 165 Oligocyclopropyl natural products, 42 Oligonucleotides, synthesis, 186 Organic solids, dynamic van der Waals forces, 156-7 Organocatalysis, proline, 29, 158 Organofluorine compounds, preparation, 152 Organometallic sesquihalides, Al, Ge, In, 58 Organometallics, C-C bond formation, Rh catalyzed, 35 molecular propeller, 86 sterically encumbered, 86 Organopalladiumcomplexes, book, 216 Organosulfur compounds, 177 Organotin complexes, 91 Organovanadium complex, pinacol coupling, 31 Organozinc carbenoids, homologation, 190 Oxadiazole preparation, 93 Oxathiacrown compounds, preparation with SCl2, 62 Oxogelsemine asymmetric preparation, 26 Palladium catalyst, heterocyclic substitution, 148 P-C bond formation, transition metal catalysts, 154 Peptide bond, cis trans isomerization, 98 Peptide encoding, combinatorial library, 78 Peptides, book, 196-8 stereoselective preparation, protease catalyst, 32 synthesis, book, 195 Peptidomimetics, 185 combinatorial library, 78 Perfluoroolefins, nucleophilic reagents, 152 Petasis reagent, for alkylidenation, 129 Phenanthroindolizidine alkaloids, 131 Phenols, ortho prenylated, preparation, 173 Phosphites, triethyl, cone angle, 85 trimethyl, cone angles, 85 Photochemistry, 138 alkenes, 142 alkynes, 142 aromatics, 143 book, 206 deexcitation, 139 Photoelimination, 146

J. Org. Chem, Vol. 68, No. 14, 2003 5803

Photolysis, carbonyl compounds, 140 Photooxidation, 144 Photophysical processes, condensed phase, 139 Photoreactions, dienones, 141 non-oxygen heteroatom compounds, 145 quinones, 141 Photoreduction, 144 Piperazines, combinatorial synthesis, 40 Piperidines, from aziridinium ring opening, 77 Polycationic organic salts, 100 Polynucleotides, synthesis, 186 Polypropionates, 164 Porphyrins, binding constants, book, 210 biochemistry and binding, book, 210 electron transfer, book, 210 NMR, EPR, book, 210 redox potentials, book, 210 synthesis, book, 210 tetrapyrrole crystal structure, book, 210 Potassium fluoride, in organic reactions, 188 Proline, amino alcohol synthesis, 72 asymmetric synthesis, 158 enantioselective Mannich reaction, 72 organocatalyst, 29 Propargylamines, R-substituted, asymmetric synthesis, 134 Proteases, in synthesis, 32 Proteins, book, 199 Pyrazinoquinazolinedione, 106 Pyrazole preparation, 93 Pyridines, combinatorial synthesis, 40 Pyrimidines, combinatorial synthesis, 40

Pyrroles, H nucleophilic substitution, 63 Pyrrolidine lactams, 69 Pyrrolidines, halomethyl, ring expansion, 77 Pyrrolizidine alkaloids, 133 Quantum tunneling, 159-60 Quinoline alkaloids, 132 Quinolizidine alkaloids, 131-2 Quinone methides, ortho-, 173 Racemic mixtures, parallel kinetic resolution, 56 Radicals, stable, main group, 38 Resolution, spontaneous, with supramolecules, 55 Ruthenium catalysis, 95 Schrock carbene, for alkylidenation, 129 Selenazines, 107 Selenazoles, 107 Selenonium dialkylamino sulfuranes, 117 Selenophenes, molecular structure, 67 Self-assembled capsules, 30 Sequential column asymmetric catalysis, 60 Sharpless asymmetric aminohydroxylation, 127 Slaframine alkaloids, 131 Solid-phase synthesis, book, 221 Solid-state diffusion, 157 Spin forbidden reactions, transition metal compounds, 57 Spirobiphenalenyl borate, 25 Spirodienone route, calixarene functionalization, 171 Spiroketal stereoselective synthesis, 108 Squalestatins, cyclization, 189 Steroids, Birch reduction, 137 Sulfonamides, ortho metalation, 161 Sulfonium dialkylamino sulfuranes, 117

5804 J. Org. Chem., Vol. 68, No. 14, 2003

Sulfuranes, dialkylaminofluoro, preparation, 117 organylfluoro, preparation, 117 Supercritical carbon dioxide, with ionic liquids, 27 Suzuki Miyaura cross coupling, 192 Synthesis, mechanisms, book, 222 tutorial, book, 207 Takeda reagent, for alkylidenation, 129 Tebbe reagent, for alkylidenation, 129 Tellurophenes, molecular structure, 67 Terpenes, synthesis, Diels-Alder, book, 201 Tetrathiomolybdate, in synthesis, 166 Thiamin diphosphate dependent enzyme, 61 Thioamides, heterocycle preparation, 36 Thiocarbonyls, N-containing, photochemistry, 115 Thiophene dioxides, 65 Tiazines, nitro derivatives, 151 Transition metal catalyst, heterocyclic substitution, 148 P-C bond formation, 154 Transmetalation, book, 211 Triazenes, in synthesis, 16 Triazine monooxides synthesis, 13 Triazole preparation, 93 Trimethylsilylethyl sulfur group, 177 Tritium labeling, 176 Vilsmeier Haack reagent, 174 Vinylcyclopropanes, rearrangement, 47 Vinyltetrazoles, 149 Zaragozic acids, total synthesis, 189 Zincke reaction, 136 JO033582M