Recent Reviews. 54 - The Journal of Organic Chemistry (ACS

Major English-language sources of critical reviews are covered. Encyclopedic treatises, annual surveys such as Specialist Periodical Reports, and comp...
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J. Org. Chem. 1999, 64, 7679-7686

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Recent Reviews. 54 compiled by Veronica M. Cornel Department of Chemistry, Reedley College, 22288 Hogan Avenue, Reedley, California 93654

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 1999 literature. Previous installment: J. Org. Chem. 1999, 64(14), 5333-40. Supporting Information Available: A file containing this Recent Reviews compilation in Microsoft Word and 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

Australian Journal of Chemistry

1. Fallis, A. G. Harvesting Diels and Alder’s Garden: Synthetic Investigations of Intramolecular [4 + 2] Cycloadditions. 1999, 32(6), 464-74. 2. Blasko, A.; Bruice, T. C. Recent Studies of Nucleophilic, General-Acid, and Metal Ion Catalysis of Phosphate Diester Hydrolysis. 1999, 32(6), 475-84. 3. Choukroun, R.; Cassoux, P. Planar Tetracoordination of Carbon in Groups 4 and 5 Organometallic Chemistry. 1999, 32(6), 494-502. 4. Diederich, F.; Kessinger, R. Templated Regioselective and Stereoselective Synthesis in Fullerene Chemistry. 1999, 32(6), 537-45. 5. Goldstein, S.; Meyerstein, D. Comments on the Mechanism of the “Fenton-Like” Reaction. 1999, 32(7), 547-50. 6. Yang, H.; Kotz, K. T.; Asplund, M. C.; Wilkens, M. J.; Harris, C. B. Ultrafast Infrared Studies of Bond Activation in Organometallic Complexes. 1999, 32(7), 551-60. 7. Bourissou, D.; Bertrand, G. The Quest for Diphosphirenium and Diphosphirenylium Salts, DiheteroatomContaining Cyclopropenium Analogs. 1999, 32(7), 56170. 8. Zipse, H. The Methylenology Principle: How Radicals Influence the Course of Ionic Reactions. 1999, 32(7), 571-8. 9. Hallis, T. M.; Liu, H.-w. Learning Nature’s Strategies for Making Deoxy Sugars: Pathways, Mechanisms, and Combinatorial Applications. 1999, 32(7), 579-88. 10. Wenthold, P. G.; Lineberger, W. C. Negative Ion Photoelectron Spectroscopy Studies of Organic Reactive Intermediates. 1999, 32(7), 597-604. 11. Jorgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Catalytic Asymmetric Addition Reactions of Carbonyls. A Common Catalytic Approach. 1999, 32(7), 605-13.

12. Eberson, L.; Hartshorn, M. P. Photochemical Nitration by Tetranitromethane. The Formation and Reactions of Adducts from the Photochemical Reactions of Aromatic Compounds with Tetranitromethane and Other X-NO2 Reagents-Invited Review. Part XLV. 1998, 51(12), 1061-81. 13. Strauss, C. R. A Combinatorial Approach to the Development of Environmentally Benign Organic Chemical Preparations. 1999, 52(2), 83-96. Canadian Journal of Chemistry 14. Fallis, A. G. 1998 Alfred Bader Award Lecture. Tangents and Targets: the Synthetic Highway from Natural Products to Medicine. 1999, 77(2), 159-77. Chemical Reviews 15. Jasat, A.; Sherman, J. C. Carceplexes and Hemicarceplexes. 1999, 99(4), 931-67. 16. Fuerstner, A. Carbon-Carbon Bond Formation Involving Organochromium(III) Reagents. 1999, 99(4), 991-1045. 17. Rubinov, D. B.; Rubinova, I. L.; Akhrem, A. A. Chemistry of 2-Acyl-1,3-Cycloalkanediones. 1999, 99(4), 1047-65. 18. Kobayashi, S.; Ishitani, H. Catalytic Enantioselective Addition to Imines. 1999, 99(5), 1069-94. 19. Mahrwald, R. Diastereoselection in Lewis-AcidMediated Aldol Additions. 1999, 99(5), 1095-120. 20. Reetz, M. T. Synthesis and Diastereoselective Reactions of N,N-Dibenzylamino Aldehydes and Related Compounds. 1999, 99(5), 1121-62. 21. Klunder, A. J. H.; Zhu, J.; Zwanenburg, B. The Concept of Transient Chirality in the Stereoselective Synthesis of Functionalized Cycloalkenes Applying the Retro-Diels-Alder Methodology. 1999, 99(5), 1163-90.

10.1021/jo994993z CCC: $18.00 © 1999 American Chemical Society Published on Web 09/15/1999

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22. Mengel, A.; Reiser, O. Around and Beyond Cram’s Rule. 1999, 99(5), 1191-223. 23. Dannenberg, J. J. Using Perturbation and Frontier Molecular Orbital Theory to Predict Diastereofacial Selectivity. 1999, 99(5), 1225-41. 24. Tomoda, S. The Exterior Frontier Orbital Extension Model. 1999, 99(5), 1243-63. 25. Cieplak, A. S. Inductive and Resonance Effects of Substituents on π-Face Selection. 1999, 99(5), 1265-336. 26. Ohwada, T. Orbital-Controlled Stereoselections in Sterically Unbiased Cyclic Systems. 1999, 99(5), 133775. 27. Gung, B. W. Structure Distortions in HeteroatomSubstituted Cyclohexanones, Adamantanones, and Adamantanes: Origin of Diastereofacial Selectivity. 1999, 99(5), 1377-86. 28. Kaselj, M.; Chung, W.-S.; Le Noble, W. J. Face Selection in Addition and Elimination in Sterically Unbiased Systems. 1999, 99(5), 1387-413. 29. Adcock, W.; Trout, N. A. Nature of the Electronic Factor Governing Diastereofacial Selectivity in Some Reactions of Rigid Saturated Model Substrates. 1999, 99(5), 1415-35. 30. Mehta, G.; Chandrasekhar, J. Electronic Control of Facial Selection in Additions to Sterically Unbiased Ketones and Olefins. 1999, 99(5), 1437-67. 31. Wipf, P.; Jung, J.-K. Nucleophilic Additions to 4,4Disubstituted 2,5-Cyclohexadienones: Can Dipole Effects Control Facial Selectivity? 1999, 99(5), 1469-80. 32. Lorsbach, B. A.; Kurth, M. J. Carbon-Carbon Bond Forming Solid-Phase Reactions. 1999, 99(6), 1549-81. 33. Raymo, F. M.; Stoddart, J. F. Interlocked Macromolecules. 1999, 99(7), 1643-63. Chemical Society Reviews 34. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Polyethynylated Cyclic π-Systems: Scaffoldings for Novel Two and ThreeDimensional Carbon Networks. 1999, 28(2), 107-19. 35. Dotz, K. H.; Tomuschat, P. Annulation Reactions of Chromium Carbene Complexes: Scope, Selectivity and Recent Developments. 1999, 28(3), 187-98. Chemistry and Industry 36. Leigh, D. A.; Murphy, A. Molecular Tailoring: The Made-to-Measure Properties of Rotaxanes. 1999, (5), 178-83. 37. Soo, E. C.; Salmon, A. B.; Lough, W. J. Separate Ways with Chiral Molecules. 1999, (6), 220-24. 38. Holmes, A. B.; Stephenson, G. R. Organic Chemistry. 1999, (6), 234-6. 39. Burgess, K. Organometallic Chemistry. 1999, (6), 236-7. Coordination Chemistry Reviews 40. Kozlowski, H.; Bal, W.; Dyba, M.; Kowalik-Jankowska, T. Specific Structure-Stability Relations in Metallopeptides. 1999, 184, 319-46. 41. Slugovc, C.; Schmid, R.; Kirchner, K. Hydridotris(pyrazolyl)borate Ruthenium ComplexessProperties and Applications. 1999, 185-6, 109-26. 42. Goh, L. Y. Polyatomic Molecules and Aggregates of Main Group 15/16 Elements in Organochromium Chemistry. 1999, 185-6, 257-76.

Recent Reviews

43. Bressan, M.; d'Alessandro, N.; Liberatore, L.; Morvillo, A. Ruthenium-Catalyzed Oxidative Dehalogenation of Organics. 1999, 185-6, 385-402. 44. Wadepohl, H. Metal Clusters and Cyclopolyenes: The Face-Capping Coordination Mode. 1999, 185-6, 551-56. Journal of Fluorine Chemistry 45. Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. Perfluorocarbon-Soluble Catalysts and Reagents and the Application of FBS (Fluorous Biphase System) to Organic Synthesis. 1999, 94(2), 183-93. Journal of Heterocyclic Chemistry 46. Makino, K.; Kim, H. S.; Kurasawa, Y. Synthesis of Pyrazoles and Condensed Pyrazoles. 1999, 36(2), 32132. 47. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. 2-Aminothiophenes by the Gewald Reaction. 1999, 36(2), 333-45. Journal of Physical Organic Chemistry 48. Exner, O. The Inductive Effect: Theory and Quantitative Assessment. 1999, 12(4), 265-74. 49. Charton, M. The Nature of Electrical Effect Transmission. 1999, 12(4), 275-82. 50. Galkin, V. I. Inductive Substituent Effects. 1999, 12(4), 283-8. Organic Preparations and Procedures International 51. Davis, F. A.; Kasu, P. V. N. Synthesis of R-Fluoro Aldehydes and Ketones. A Review. 1999, 31(2), 125-45. 52. Gao, H.; Dias, J. R. Selective Protection of the Various Hydroxy Groups of Cholic Acid and Derivatives. A Review. 1999, 31(2), 145-66. Organic Reactions 53. Luzzio, F. A. The Oxidation of Alcohols by Modified Oxochromium(VI)-Amine Reagents. 1998, 53, 1-221. 54. Rickborn, B. The Retro-Diels-Alder Reaction. Part II. Dienophiles with One or More Heteroatom. 1998, 53, 223-629. Progress in Nuclear Magnetic Resonance Spectroscopy 55. Buchanan, G. W. Nuclear Magnetic Resonance Studies of Crown Ether. 1999, 34(3,4), 327-77. Progress in the Chemistry of Organic Natural Products 56. Gournelis, D. C.; Laskaris, G. G.; Verpoorte, R. Cyclopeptide Alkaloids. 1998, 75, 1-179. Pure and Applied Chemistry 57. Heinemann, C.; Xing, X.; Warzecha, K.-D.; Ritterskamp, P.; Gorner, H.; Demuth, M. An Asymmetric Induction Principle and Biomimetics with Photons via Electron Transfer. 1998, 70(11), 2167-76.

Recent Reviews

58. Wirz, J. Kinetics of Proton-Transfer Reactions Involving Carbon. 1998, 70(11), 2221-32. 59. Sessler, J. L.; Anzenbacher, P., Jr.; Jursikova, K.; Miyaji, H.; Genge, J. W.; Tvermoes, N. A.; Allen, W. E.; Shriver, J. A.; Gale, P. A.; Kral, V. Functionalized Calix[4]pyrroles. 1998, 70(12), 2401-8. Reviews on Heteroatom Chemistry 60. Ishii, A.; Nakayama, J. Cyclic Oligosulfides, RR′CSn: From the Medium to the Smallest (n ) 2) Ring. 1998, 19, 1-34. 61. Fuchigami, T.; Higashiya, S.; Hou, Y.; Dawood, K. M. Highly Selective Direct and Indirect Anodic Monofluorination of Heterocyclic Compounds. 1998, 19, 6778. 62. Ishida, H.; Inoue, Y. Peptides that Contain Unnatural Amino Acids: Toward Artificial Proteins. 1998, 19, 79-142. 63. Kielbasinski, P. Enzyme-Promoted Syntheses of Chiral, Non-racemic Heteroorganic Compounds with a Sole Stereogenic Center on the Heteroatom. 1998, 19, 143-72. 64. Yamada, S. Chemistry of Highly Twisted Amides. 1998, 19, 203-36. 65. Uneyama, K. An Electrochemical Approach to the Syntheses of Fluorinated Organic Compounds. 1999, 20, 1-27. 66. Ohno, A. Designed Syntheses of Chiral Compounds Mediated by Biocatalysts: Production of a Desired Stereoisomer. 1999, 20, 29-68. 67. Kim, Y. H.; Yang, S. G. Organic Synthesis Utilizing Tetrabutylammonium Peroxydisulfate. 1999, 20, 69-96. 68. Tada, M. Reactions of Alkyl-Cobalt Complexes. 1999, 20, 97-144. 69. Yasui, S.; Okamura, M.; Fujii, M. Multistep Mechanism for “Hydride” Transfer in the Redox Reactions Induced by NAD(P)H and NAD(P)+ Models. 1999, 20, 145-65. 70. Fujii, M.; Yasui, S.; Nakamura, K. Silica Gel Catalyzed Selective Reductions by NAD(P)H Models. 1999, 20, 167-205. 71. Mikata, Y.; Okamura, M. Mechanism and Stereochemistry in the Reaction of NAD(P)H Model Compounds: Conversion from Central into Axial Chirality. 1999, 20, 207-26. 72. Yamanoi, Y.; Imamoto, T. New Chiral Phosphine Ligands for Catalytic Asymmetric Reactions. 1999, 20, 227-48. 73. Satoh, N.; Fukuzumi, S. Electron-Transfer Chemistry of 10-Methylacridinium Ion. 1999, 20, 249-81. 74. Shiraki, R.; Tadano, K. Synthetic Studies of Highly Functionalized γ-Lactam Natural Products, PI-091 and Epolactaene. 1999, 20, 283-307. Russian Chemical Reviews 75. Aleksandrovich, B. V.; Pavlovna, P. M. Cationic Molecular Rearrangements of Natural Terpene Compounds in Superacidic Media: Reality and Predictions. 1999, 68(5), 393-414. 76. Dzhafarovich, S. I.; Iskhakovich, U. A.; Dmitrievich, G. A. Synthesis, Reactions and Structures of Complexes of Metal Carbonyls and Cyclopentadienyl Carbonyls with Organotellurium Ligands. 1999, 68(5), 415-33.

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77. Georgievich, N. V.; Viktorovich, S. A.; Sergeevna, B. E. Methods for the Synthesis of R,β-Unsaturated Trifluoromethyl Ketones and Their Use in Organic Synthesis. 1999, 68(6), 483-505. 78. Korostova, S. E.; Trofimov, B. A.; Mikhaleva, A. I. Bipyrroles, Furyl- and Thienylpyrroles. 1999, 68(6), 50631. 79. Fedorovich, N. A.; Anatol′evna, K. G. C-Alkenylation of Pyrimidine Nucleosides and Their Analogues. 1999, 68(6), 532-54. 80. Alekseevich, R. O. Descriptors of Molecular Structure in Computer-Aided Design of Biologically Active Compounds. 1999, 68(6), 555-76. 81. Evkhononovich, E. M. Expert Systems for the Determination of Structures of Organic Molecules by Spectral Methods. 1999, 68(7), 579-604. 82. Grigor′evich, S. A. High-Resolution Solid State NMR Spectroscopy in the Studies of Hydrocarbons and Alcohols Conversions on Zeolites. 1999, 68(7), 619-37. 83. Grigor′evna, L. G.; Ivanovna, D. T.; Borisovich, R. I.; Nikolaevna, M. A. N-Functionally Substituted Imines of Polychlorinated (Brominated) Aldehydes and Ketones. 1999, 68(7), 638-62. 84. Vladimirovich, A. A.; Stanislavovich, R. I.; Aleksandrovich, K. N. Combustion of Char-forming Polymeric Systems. 1999, 68(7), 663-73. 85. Mikhailovna, D. A. Transformations of Organic Compounds Under the Action of Mechanical Stress. 1999, 68(8), 708-24. 86. Georgievich, F. G.; Aleksandrovich, F. A. N-Flouroamines and Their Analogues as Fluorinating Agents in Organic Synthesis. 1999, 68(8), 725-59. 87. L′vovich, R. A.; Anatol′evna, S. T.; Myullen K. New Condensation Polymers Having Low Dielectric Constants. 1999, 68(8), 760-72. 88. Feliksovich, G. A. New Insecticides and Acaricides. 1999, 68(8), 773-84. Sulfur Reports 89. Maier, G.; Reisenauer, H. P.; Ruppel, R. Matrix Isolation of Chalcogeno Heterocumulenes. 1999, 21(4), 335-55. 90. Flammang, R.; Wentrup, C. Mass Spectrometry of S:C:(C)n:C:X Cumulenes. 1999, 21(4), 357-71. 91. Janoschek, R. Theoretical Studies on Heterocumulated Double Bond Systems. 1999, 21(4), 373-400. 92. Saito, S. Sulfur-Bearing Carbon-Chain Molecules in Space and in the Laboratory. 1999, 21(4), 401-21. 93. Stadlbauer, W.; Kappe, T. The Chemistry of Carbon Subsulfide. 1999, 21(4), 423-45. Synlett 94. Rodriguez, J. Our Recent Contribution to the Field of Anionic Domino Transformations. 1999, (5), 505-18. 95. Jung, I. N.; Yoo, B. R. Lewis Acid-Catalyzed Regioand Stereoselective Allylsilation of Simple Unsaturated Hydrocarbons. 1999, (5), 519-28. 96. Gielen, H. Polyamino Acids. 1999, (5), 656. 97. Bruckner, R.; Suffert, J. The Bis(enol triflate) Route to Dienediyne Models of the Biradical Forming and DNACleaving Natural Product Neocarzinostatin Chromophore. 1999, (6), 657-79. 98. Butenschon, H. π-Complexes with Annelated Cyclobutene Rings. Bicyclo[3.2.0]heptadienyl Anion and

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Benzocyclobutene as Ligands for Transition Metals. 1999, (6), 680-91. 99. Jaschke, A.; Frauendorf, C.; Hausch, F. In Vitro Selected Oligonucleotides as Tools in Organic Chemistry. 1999, (6), 825-33. 100. Pfaltz, A. From Corrin Chemistry to Asymmetric Catalysis. A Personal Account. 1999, (special issue), 83542. 101. Jung, M. E. New Gem- and Vic-Disubstituent Effects on Cyclizations. 1999, (special issue), 843-6. 102. Denmark, S. E.; Wu, Z. The Development of Chiral, Nonracemic Dioxiranes for the Catalytic, Enantioselective Epoxidation of Alkenes. 1999, (special issue) 847-59. 103. Ballini, R. Recent Progress on the Ring Cleavage of Cyclic 2-Nitro Ketones by External Nucleophiles. 1999, (7), 1009-18. 104. Griesbeck, A. G.; Kramer, W.; Oelgemoller, M. Synthetic Applications of Photoinduced Electron-Transfer Decarboxylation Reactions. 1999, (7), 1169-78. 105. Fernandez-Megia, E. Zirconocene Hydrochloride, “Schwartz reagent”. 1999, (7), 1179. SynthesissStuttgart 106. Ruck-Braun, K.; Mikulas, M.; Amrhein, P. Organoiron Compounds for Selective Organic Transformations. 1999, (5), 727-44. 107. Broggini, G.; Zecchi, G. Pyrrolizidine and Indolizidine Syntheses Involving 1,3-Dipolar Cycloadditions. 1999, (6), 905-17. 108. Butenandt, J.; Burgdorf, L. T.; Carell, T. Synthesis of DNA Lesions and DNA-Lesion-Containing Oligonucleotides for DNA-Repair Studies. 1999, (7), 1085-105. Tetrahedron 109. Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Organocerium Compounds in Synthesis. 1999, 55(13), 3803-30. 110. Dieter, R. K. Reaction of Acyl Chlorides with Organometallic Reagents: A Banquet Table of Metals for Ketone Synthesis. 1999, 55(14), 4177-236.

111. Rigby, J. H. Chromium(0)-Promoted Higher-Order Cycloaddition Reactions in Organic Synthesis. 1999, 55(15), 4521-38. 112. James, I. W. Linkers for Solid-Phase Organic Synthesis. 1999, 55(16), 4855-946. 113. Toyota, M.; Ihara, M. Total Synthesis of Aphidicolane and Stemodane Diterpenes. 1999, 55(18), 564179. 114. Yang, H. W.; Romo, D. Methods for the Synthesis of Optically Active β-Lactones (2-Oxetanones). 1999, 55(21), 6403-34. 115. Rajappa, S. Nitroenamines: An Update. 1999, 55(23), 7065-114. Topics in Current Chemistry 116. De Meijere, A.; Kozhushkov, S. I. Macrocyclic Structurally Homoconjugated Oligoacetylenes: Acetylene- and Diacetylene-Expanded Cycloalkanes and Rotanes. 1999, 2011-42. 117. Diederich, F.; Gobbi, L. Cyclic and Linear Acetylenic Molecular Scaffolding. 1999, 201, 43-79. 118. Haley, M. M.; Pak, J. J.; Brand, S. C. Macrocyclic Oligo(phenylacetylenes) and Oligo(phenyldiacetylenes). 1999, 201, 81-130. 119. Bunz, U. H. F. Carbon-Rich Molecular Objects from Multiply Ethynylated π-Complexes. 1999, 201, 13161. 120. Scherf, U. Oligo- and Polyarylenes, Oligo- and Polyarylenevinylenes. 1999, 201, 163-222. Topics in Stereochemistry 121. Mislow, K. Molecular Chirality. 1999, 22, 1-82. 122. Hilvert, D. Stereoselective Reactions with Catalytic Antibodies. 1999, 22, 83-135. 123. White, J. M.; Clark, C. I. Stereoelectronic Effects of Group IVA Metal Substituents in Organic Chemistry. 1999, 22, 137-200. 124. Shibasaki, M.; Sasai, H. Asymmetric Catalysis with Chiral Lanthanoid Complexes. 1999, 22, 201-25. 125. Fenwick, D. R.; Kagan, H. B. Asymmetric Amplification. 1999, 22, 257-96.

Contributed Volumes Advances in Medicinal Chemistry. Volume 4. Maryanoff, B. E., Reitz, A. B., Eds. JAI Press: Stamford, Connecticut, 1999. 126. Obrecht, D.; Altorfer, M.; Robinson, J. A. Novel Peptide Mimetic Building Blocks and Strategies for Efficient Lead Finding. 127. Ojima, I.; Kuduk, S. D.; Chakravarty, S. Recent Advances in the Medicinal Chemistry of Taxoid Anticancer Agents. 128. Ferguson, A. M.; Cramer, R. D. Design of Compound Libraries for Detecting and Pursuing Novel Small Molecule Leads. 129. Williams, T. M.; Dinsmore, C. J. Farnesyl Transferase Inhibitors: Design of a New Class of Cancer Chemotherapeutic Agents. Advances in Metal-Organic Chemistry. Volume

6. Liebeskind, L. S., Ed. JAI Press: Stamford, Connecticut, 1998. 130. Echavarren, A. M.; Castano, A. M. Oxa- and Azametallacycles of Nickel: Fundamental Aspects and Synthetic Applications. 131. Lautens, M.; Tam, W. Transition Metal Catalyzed Cycloaddition Reactions of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes). 132. Spencer, J.; Pfeffer, M. State of the Art in Selective Hetero- and Carbocyclic Syntheses Mediated by Cyclometalated Complexes. 133. Liu, R.-S. Synthetic Application of Cyclopentadienyl Molybdenum(II)- and Tungsten(II)-Allyl and Diene Compounds in Organic Synthesis. 134. Miyaura, N. Synthesis of Biaryls via the CrossCoupling Reaction of Arylboronic Acids.

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Advances in Nitrogen Heterocycles. Volume 3. Moody, C. J., Ed. JAI Press: Stamford, Connecticut, 1998. 135. Hodges, L. M.; Harman, W. D. The Activation and Manipulation of Pyrroles by Pentaammineosmium(II). 136. Edstrom, E. D. Synthesis of [β]-Annelated Pyrroles via an Acylation Approach. 137. Black, D. S. Applications of Iminium Cation Chemistry to Activated Indoles. 138. Beall, L. S.; Padwa, A. Application of Nitrogen Ylide Cyclizations for Organic Synthesis 1998. 139. Wood, M. E.; Fryer, A. M. Synthesis of Kainoids and Kainoid Analogs. Advances in Strained and Interesting Organic Molecules. Volume 7. Halton, B., Ed. JAI Press: Stamford, Connecticut, 1999 140. Tsanaktsidis, J. Polysubstituted Cubanes: Towards Complete Systematic Substitution of the Cubane Nucleus. 141. Warrener, R. N. A Personal Perspective on Norbornenes, Cyclobutenes, and Other Ring-Strained Dienophiles in Organic Synthesis. 142. Mehta, G.; Rao, H. S. P. Synthetic Studies Related to Fullerenes and Fullerene Fragments. Advances in Supramolecular Chemistry. Volume 5. Gokel, G. W., Ed. JAI Press: Stamford, Connecticut, 1999. 143. Schneider, S. E.; Anslyn, E. V. Molecular Recognition and Solid Phase Organic Synthesis: Synthesis of Unnatural Oligomers, Techniques for Monitoring Reactions, and the Analysis of Combinatorial Libraries. Advances in Theoretically Interesting Molecules.

Volume. Thummel, R. P., Ed. JAI Press: Stamford, Connecticut, 1998. 144. Wege, D. Aspects of the Chemistry of Isobenzofurans: Bridging the Gap Between Theoretically Interesting Molecules and Natural Products. 145. Cory, R. M.; McPhail, C. L. Fascinating Stops on the Way to Cyclacenes and Cyclacene Quinones: A Tour Guide to Synthetic Progress to Date. 146. Kuck, D. Benzoannelated Fenestranes. 147. Williams, R. V. SemibullvalenessHomoaromatic Bovines. 148. Gilbert, J. C.; Kirschner, S. Cyclopentynes: Enigmatic Intermediates. 149. Biedermann, P. U.; Stezowski, J. J.; Agranat, I. Overcrowded Polycyclic Aromatic Enes. Alkaloids: Chemical and Biological Perspectives. Volume 13. Pelletier, S. W., Ed. Elsevier: Amsterdam, The Netherlands, 1999. 150. Ojima, I.; Iula, D. M. New Approaches to the Syntheses of Piperidine, Izidine, and Quinazoline Alkaloids by Means of Transition Metal Catalyzed Carbonylations. 151. LeQuesne, P. W.; Dong, Y.; Blythe, T. A. Recent Research on Pyrrole Alkaloids. 152. Anthoni, U.; Christophersen, C.; Nielson, P. H. Naturally Occurring Cyclotryptophans and Cyclotryptamines. 153. Joshi, B. S.; Pelletier, S. W. Recent Developments in the Chemistry of Norditerpenoid and Diterpenoid Alkaloids. 154. Daly, J. W.; Garraffo, H. M.; Spande, T. F. Alkaloids from Amphibian Skins.

Monographs 155. Barcelo, D., Ed. Special Issue on Molecular Imprints and Related Approaches for Solid-Phase Extraction and Sensors in Chemical Analysis. [In: Trends Anal. Chem. 1999, 18(3)]. Elsevier: Amsterdam, The Netherlands, 1999. 156. Blitz, J. P.; Little, C. B. Fundamental and Applied Aspects of Chemically Modified Surfaces. Royal Society of Chemistry: Cambridge, U.K., 1999. 157. Bunz, U. H. F.; Adams, R. D., Eds. Special Volume: Carbon-Rich Organometallics. [In: J. Organomet. Chem. 1999, 578(1-2)]. Elsevier: Lausanne, Switzerland, 1999. 158. Dyson, N. A. Chromatographic Integration Methods. Humana Press: Totowa, NJ, 1998. 159. Freeman, J. P. Organic Syntheses Collective Volumes. Vol. 9. Wiley: New York, 1998. 160. Fu¨rstner, A., Ed. Alkene Metathesis in Organic Synthesis. [In: Top. Organomet. Chem., 1998, 1]. Springer: Berlin, Germany, 1998. 161. Gadamasetti, K. G., Ed. Process Chemistry in the Pharmaceutical Industry. Marcel Dekker: New York, 1999. 162. Grunanger, P.; Vita-Finzi, P. Isoxazoles, Part 2. [In: Chem. Heterocycl. Compd. 1999, 49(Part 2)]. John Wiley & Sons: Chichester, U.K., 1999.

163. Hanai, T. HPLC: A Practical Guide. Royal Society of Chemistry: Cambridge, U.K., 1999. 164. Harwood, L. M.; Percy, J. Experimental Organic Chemistry: Preparative and Microscale, 2nd ed. Blackwell Scientific: Oxford, U.K., 1998. 165. Hayashi, T.; Tomioka, K.; Yonemitsu, O., Eds. Asymmetric Synthesis: Graphical Abstracts and Experimental Methods. Gordon & Breach: New York, 1998. 166. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed. University Science Books: Sausalito, CA, 1999. 167. Kier, L. B.; Hall, L. H. Molecular Structure Description. The Electrotopological State. Academic Press: San Diego, CA, 1999. 168. Knochel, P., Joned, P., Eds. Organozinc Reagents: A Practical Approach. Oxford University Press: Oxford, U.K., 1999. 169. Leszczynski, J., Ed. Computational Molecular Biology. Elsevier: Amsterdam, The Netherlands, 1999. 170. Miertus, S., Fassina, G., Eds. Combinatorial Chemistry and Technology. Principles, Methods, and Applications. Marcel Dekker: New York, 1999. 171. Mulzer, J.; Waldmann, H., Eds. Organic Synthesis Highlights III. Wiley-VCH: Weinheim, Germany, 1998.

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172. Palyi, G.; Zucchi, C.; Caglioti, L. E. Advances in Biochirality. Elsevier: Amsterdam, The Netherlands, 1999. 173. Pomogailo, A. D. Catalysis by Polymer-Immobilized Metal Complexes. Gordon & Breach: New York, 1998. 174. Sainsbury, M., Ed. Second Supplements to the 2nd Edition of Rodd’s Chemistry of Carbon Compounds, Second Supplement to Volume IV Heterocyclic Compounds, Part G: Six-membered Heterocyclic Compounds with (a) a Single Nitrogen Atom in the Ring: Polycyclic Fused Ring Compounds, (b) an Atom of Phosphorus, Arsenic, Antimony or Bismuth; Part H: Six-membered Fused-Ring Heterocyclic Compounds with a Single Nitrogen Atom in the Ring. Elsevier: Amsterdam, The Netherlands, 1998. 175. Sainsbury, M., Ed. Second Supplements to the 2nd Edition of Rodd’s Chemistry of Carbon Compounds. Vol. IV, Parts K (partial) and L. Heterocyclic Compounds

Recent Reviews

Part: 6-membered Heterocycles with 2 or more Heteroelements, 1 or more from Groups II/III/IV/V/VII. Heterocycles with 7 or more Ring Atoms; Fused-ring Heterocyclic Compounds with 3 or more Nitrogen Atoms; Purines and related ring systems; Nucleosides, Nucleotides and Nucleic Acids; Pteridines, Alloxazines, Flavins, related compounds. The Biosynthesis of Plant Alkaloids, Nitrogenous Microbes. Elsevier: Amsterdam, The Netherlands, 1999. 176. Togni, A.; Halterman, R. L. Metallocenes. Wiley: New York, 1998. 177. Whitaker, J., R., Shahidi, F., Munguia, A. L., Yada, R. Y., Fuller, G., Eds. Functional Properties of Proteins and Lipids. American Chemical Society: Washington, DC, 1998. 178. Yamamoto, Y., Negishi, E., Eds. Recent Advances in Organopalladium Chemistry: Dedicated to Professors Jiro Tsuji and Richard F. Heck. [In: J. Organomet. Chem. 1999, 576(1-2)]. Elsevier: Lausanne, Switzerland, 1999.

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Index Acaricides, 88 Acetylenic molecular scaffolding, 117 Acylcycloalkanedione, enol ether, preparation, 17 ester enol, preparation, 17 Adamantane, heteroatom-substituted, 27 sterochemistry, book, 29 Adamantanone, heteroatom-substituted, 27 Alcohol conversion, over zeolites, NMR, 82 Alcohol oxidation, with oxochromium amine, 53 Aldehyde, dibenzylamino, 20 R-fluoro, 51 polychlorinated, imines, 83 Aldol reaction, diastereoselection, 19 with Lewis acids, 19 Alkaloids, cyclopeptide, 56 diterpenoid, book, 153 from amphibians, book, 154 indolizidine, synthesis, 107 izidine, book, 150 norditerpenoid, book, 153 piperidine, book, 150 plant, biosynthesis, book, 175 pyrrole, book, 151 pyrrolidine, synthesis, 107 quinazoline, book, 150 Alkenes, enantioselective epoxidation, 102 metathesis, 160, 171 Alkyl cobalt complexes, 68 Alkylation, drugs, using solid phase extraction, book, 156 Allylsilylation, 95 Amides, highly twisted, 64 Amino acids, artificial, 62 Aminothiophenes, Gewald preparation, 47 Ammonium tetrabutyl peroxydisulfate, 67 Antibodies, in reactions, 122 on silica, book, 156 Anticancer agents, taxoid, 127 Antitumor agents, 129 Aromatic alkenes, hindered polycyclic, book, 149 Aromatics, photochemical nitration, 12 Asymmetric addition, carbonyl catalysts, 11 Asymmetric amplification, 125 Asymmetric catalysis, 100 with chiral lanthanoids, 124 with chiral phosphines, 72 Asymmetric synthesis, biocatalysts, 66 book, 165 drugs, book, 161 Biaryl preparation, from arylboronic acids, 134 Bicycloheptadienyl ligands, 98 Biocatalysis, chiral compounds, 66 Biomimetics, electron transfer, 57 Bipyrroles, 78 Calixpyrroles, 59 Carbon subsulfides, 93 Carbon, planar tetracoordinate, 3 Carbon-hydrogen bond activation, IR, 6 Carceplexes, 15 Catalysts, palladium, book, 166 polymer-immobilized metal complexes, book, 173

Catalysts, stereoselective, antibodies, 122 Chiral compounds, using biocatalysts, 66 Chirality, 37, 121 biological, book, 172 Cholic acid, hydroxy group protection, 52 Chromatography, integration, book, 158 Chromium carbenes, annulation, 35 Combinatorial chemistry, book, 170 deoxysugar reaction, 9 macrolide antibiotics, 9 nucleic acid synthesis, 143 transition metals, book, 166 Combinatorial libraries, 128 book, 170 environmentally friendly, 13 Computational chemistry, biomolecules, book, 169 nucleic acids, book, 169 Corrin chemistry, 100 Cram’s rule, 22 Crown ethers, NMR, 55 Cubanes, substituted, 140 Cumulenes, thioketone, mass spectrometry, 90 Cyclacenes, 145 Cyclic systems, sterically unbiased, 26 Cycloaddition, chromium promoted, 111 geminal disubstituent effect, 101 intramolecular, 101 Cycloalkanedione, acyl, preparation ester enol, 17 cyclic ketone, 17 Cycloalkanes, acetylene-expanded, 116 stereoselective synthesis, 21 Cyclobutenes, 141 Cyclohexadienones, nucleophilic addition, 31 Cyclohexanones, heteroatom substituted, 27 Cyclopentadienyliron, 106 Cyclopentynes, intermediates, 148 Cyclopolyene, 44 Cyclotryptamines, book, 152 Cyclotryptophans, book, 152 Deoxysugars, synthesis, 9 Diastereofacial selectivity, 23, 29 Diels-Alder reaction, 1 Dienophiles, ring strained, 141 Dihydropyridines, 70 Dioxiranes, chiral, alkene epoxidation, 102 Diphosphirenium salts, 7 Diphosphirenylium salt, 7 Diterpenes, aphidicolane, 113 stemodane, 113 DNA lesions, synthesis, 108 Domino transformations, anionic, 94 Drug development, book, 161 Drug discovery, book, 161 Electrochemical reactions, 65 Electrotopological state, book, 167 Enamines, nitro-, 115 Enzymes, chiral compounds, 66 mechanical inactivation, 85 Expert systems, spectroscopy, 81 Face selection, cyclohexadienones, 31 inductive resonance, 25 resonance effect, 25 substituent effect, 25 Farnesyl transferase inhibitors, 129 Fenestranes, benzoannelated, 146 Fenton reaction, mechanism, 5

Fluorination, 65 with fluoramines, 86 Fluoroamines, N-, 86 Fluorous biphase systems, in synthesis, 45 Frontier molecular orbital theory, 23 Frontier orbital extension model, 24 Fullerenes, 142 regioselective preparation, 4 stereoselective preparation, 4 Geminal disubstituent effect, cycloaddition, 101 Haloarenes, dehalogenation, 43 Hemicarceplexes, 15 Heterocumulenes, chalcogeno, 89 Heterocycles, anodic fluorination, 61 eight-membered rings, book, 175 more than eight-membered rings, book, 175 phosphorus-containing, 7 six-membered rings, book, 174 synthesis, with cyclometalated complexes, 132 Heteroorganics, enzyme-promoted synthesis, 63 stereselective synthesis, 63 Heteropolyacetylenes, 91 Homochirality, biomolecules, book, 172 Homogeneous catalysts, book, 166 HPLC, book, 163 Hydrocarbon conversion, over zeolites, NMR studies, 82 Imines, reductive amination, 18 stereoselective addition, 18 Indole preparation, via iminium cations, 137 Inductive effect, 48, 50 Insecticides, 88 Intermediates, negative ion photoelectron spectroscopy, 10 Ionic reactions, substituent effect, 8 Isobenzofurans, 144 Isoprenoids, polyalkene radicals, 57 Isoxazoles, book, 162 Kainoids, hydroxyproline synthon, 139 preparation, 139 Ketones, cumulenic, matrix spectra, 89 cyclic 2-nitro, ring cleavage, 103 R-fluoro, 51 polychlorinated, imines, 83 stereochemical addition, 30 synthesis, with acyl chlorides, 110 trifluoromethyl, unsaturated, 77 Lactones, β-, optically active, 114 Macrocycles, oligoacetylene, 116 oligophenylacetylenes, 118 Macromolecules, interlocked, 33 Metal clusters, face capping, 44 Metallocenes, 176 Metallopeptides, structure stability, 40 Methylacridinium ion, redox catalyst, 73 Methylenol principal radical, 8 Microscale organic chemistry, 164 Molecular design, descriptors, 80 Molecular imprints, book, 155 Natural products, epolactaene, 74 in medicine, enediynes, 14 γ-lactam, 74 Neocarzinostatin chromophore, dienediyne model, 97 Nickelacycle amino acid synthon, 130

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Nicotinamide adenine dinucleotide model, 69-71 Nitro enamines, 115 Nitrogen ylides, cyclization, 138 NMR, crown ethers, 55 Norbornadienes, cycloaddition, 131 Norbornenes, 141 Nucleic acids, solid-phase synthesis, 143 Nucleosides, pyrimidine, C-alkenyl, 79 Nucleotides, book, 175 Olefin, stereochemical addition, 30 Oligonucleotides, catalysts, 99 with DNA lesions, 108 Oligophenylacetylene, 118 Oligophenyldiacetylene, 118 Oligosulfides, cyclic, 60 Organocerium compounds, 109 Organochromium complexes, polyatomic, 42 Organochromium reagent, carbon bond formation, 16 Organocobalt complexes, 68 Organofluorine compounds, 65 Organoiron compounds, 106 Organometallic chemistry, 39 Organometallic reaction mechanisms, book, 166 Organometallics, bond activation, IR, 6 carbon-rich, 157 Organopalladium complexes, 178 Organoruthenium complexes, 41 Organosulfur hydrocarbons, prepared in space, 92 Organotellurium complexes, 76 Organozinc reagents, 168 Oxazoline chiral ligands, 100 Peptides, artificial, 62 mimetics, 126 Peptidomimetic building blocks, 126 Perfluorocarbon soluble catalysts, 45 Phase-transfer catalysis, drug synthesis, book, 161 Phosphate diester hydrolysis, catalysts, 2 Phosphine ligands, chiral, 72 Photochemistry, asymmetric induction, 57 Photoinduced decarboxylation, 104

Phthalocyanines, on surfaces, book, 156 π-Complexes, ethynylated, 119 Pinacol coupling, organochromium reagent, 16 Polyamino acids, asymmetric epoxidation, 96 Polyarylenes, 120 Polyarylenevinylenes, preparation, 120 Polycyclic fused-ring compounds, book, 174 Polyethynylated cyclic π-system, 34 Polymers, char formation, 84 condensation, 87 grafted onto surfaces, book, 156 mechanical stress, 85 transition metal catalysts, book, 166 Propadienedithiones, 93 Proteins, artificial, 62 flax, acylation, book, 177 food functionalality, book, 177 mechanical stress, 85 surface activity, book, 177 Proton-transfer reactions, carbon, 58 Pteridines, book, 175 Purines, book, 175 Pyrazoles, 46 Pyrroles, 78 activation, pentaammineosmium, 135 annelated, preparation, 136 Pyrrolidine, synthesis, dipolar cycloaddition, 107 Quinones, cyclacenes, 145 Reformatskii reaction, organochromium reagent, 16 Retro-Diels-Alder reaction, 21 heteroatom dienophile, 54 Rotanes, acetylene-expanded, 116 Rotaxane, 36 Ruthenium catalysts, oxidative dehalogenation, 43 Schwartz reagent, 105 Self-assembly, microstructures, on surfaces, book, 156 Semibullvanes, book, 147 Silicon-hydrogen bond activation, IR, 6 Soilid-phase synthesis, book, 170

Recent Reviews carbon bonds, 32 linkers, 112 Solid-phase extraction, book, 155 Spectroscopy, expert systems, 81 Stereochemical addition, 28 Stereochemistry, electronic factors, 29 Stereochemical elimination, 28 Stereoelectronic effect, group IVA elements, 123 Stereoselection, orbital controlled, 26 Stereoselectivesynthesis,transientchirality, 21 Stereoselectivity, π-facial, 24-5 Stilbenes, donor-acceptor substituted, book, 156 Structure-activity models, book, 167 Substituent effect, group IVA elements, 123 Surfaces, modification, book, 156 Synthesis, 38 book, 159, 171 with molybdenum-allyl compounds, 133 with molybdenum dienes, 133 with tungsten-allyl compounds, 133 with tungsten dienes, 133 Synthons, hydroxyproline, 139 Taxoid anticancer agents, 127 Terpenes, molecular rearrangement, 75 Terpenoids, polycyclic, preparation, 57 Tetrabutylammonium peroxydisulfate, 67 Tetrahydrofuranylation, 67 Tetranitromethane, nitration of aromatics, 12 Thioketene cumulenes, mass spectrometry, 90 Thioketones, matrix isolation, 89 Transition metal complexes, in synthesis, book, 166 Transition metal hydrides, book, 166 Transmission, electric, inductive effect, 49 Zeolites, in reactions, NMR, 82 Zirconocene hydrochloride, 105 JO994993Z