Number 70 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(14), 5795-804. 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. Casnati, A.; Sansone, F.; Ungaro, R. Peptido- and Glycocalixarenes: Playing with Hydrogen Bonds around Hydrophobic Cavities. 2003, 36(4), 246-54. 2. Garcia-Garibay, M. A. Engineering Carbene Rearrangements in Crystals: From Molecular Information to Solid-State Reactivity. 2003, 36(7), 491-8. 3. Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Asymmetric Photoreactions within Zeolites: Role of Confinement and Alkali Metal Ions. 2003, 36(7), 509-21. 4. Adam, W.; Trofimov, A. V. Viscosity as an Experimental Tool in Studying the Mechanism of Stereoselective and Product-Selective Chemical Transformations Through Frictional Impositions. 2003, 36(8), 571-9. 5. Galli, C.; Rappoport, Z. Unequivocal SRN1 Route of Vinyl Halides with a Multitude of Competing Pathways: Reactivity and Structure of the Vinyl Radical Intermediate. 2003, 36(8), 580-7. 6. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry. 2003, 36(8), 621-30. 7. Nassimbeni, L. R. Physicochemical Aspects of HostGuest Compounds. 2003, 36(8), 631-7. Advanced Synthesis and Catalysis 8. Knowles, W. S. Asymmetric Hydrogenations (Nobel Lecture 2001). 2003, 345(1+2), 3-13.
9. Noyori, R. Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001). 2003, 345(1+2), 15-32. 10. Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hormann, E.; McIntyre, S.; Menges, F.; Schonleber, M.; Smidt, S. P.; Wustenberg, B.; Zimmermann, N. Iridium-Catalyzed Enantioselective Hydrogenation of Olefins. 2003, 345(1+2), 33-44. 11. Studer, M.; Blaser, H.-U.; Exner, C. Enantioselective Hydrogenation using Heterogeneous Modified Catalysts: an Update. 2003, 345(1+2), 45-65. 12. Crepy, K. V. L.; Imamoto, T. Recent Developments in Catalytic Asymmetric Hydrogenation Employing PChirogenic Diphosphine Ligands. 2003, 345(1+2), 79-101. 13. Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments. 2003, 345(1+2), 103-51. Aldrichimica Acta 14. Lauret, C.; Roberts, S. M. Asymmetric Epoxidation of R,β-Unsaturated Ketones Catalyzed by Poly(Amino Acids). 2002, 35(2), 47-51. 15. Kanth, J. V. B. Borane-Amine Complexes for Hydroboration. 2002, 35(2), 57-66. Angewandte Chemie, International Edition in English 16. Westermann, B. Asymmetric Catalytic Aza-Henry Reactions Leading to 1,2-Diamines and 1,2-Diaminocarboxylic Acids. 2003, 42(2), 151-3.
10.1021/jo033583e CCC: $25.00 © 2003 American Chemical Society
Published on Web 09/26/2003
J. Org. Chem. 2003, 68, 7929-7936
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17. Cardenas, D. J. Advances in Functional-GroupTolerant Metal-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions. 2003, 42(4), 384-7. 18. Murakami, M. New Catalyzed Three-Component Cycloadditions for the Synthesis of Eight-Membered Carbocycles. 2003, 42(7), 718-20. 19. Lenoir, D. The Electrophilic Substitution of Arenes: Is the π Complex a Key Intermediate and What is its Nature? 2003, 42(8), 854-7. 20. Duthaler, R. O. Proline-Catalyzed Asymmetric R-Amination of Aldehydes and Ketones-An Astonishingly Simple Access to Optically Active R-Hydrazino Carbonyl Compounds. 2003, 42(9), 975-8. 21. Hoffmann, R. W. Meso Compounds: Stepchildren or Favored Children of Stereoselective Synthesis? 2003, 42(10), 1096-109. 22. Grimes, R. N. Supercarboranes. 2003, 42(11), 1198-200. 23. Schafer, M. Supramolecular Crown Ether Adducts in the Gas Phase: From Molecular Recognition of Amines to the Covalent Coupling of Host/Guest Molecules. 2003, 42(17), 1896-9. 24. Kirmse, W. Persistent Triplet Carbenes. 2003, 42(19), 2117-9. Australian Journal of Chemistry 25. Kanno, K.; Kawazumi, H.; Miyazaki, M.; Maeda, H.; Fujii, M. Enhanced Enzymatic Reactions in a Microchannel Reactor. 2002, 55(11), 687-90. 26. McGowan, G. Applications of the [2,3]-Wittig Rearrangement to Total Synthesis. 2002, 55(12), 799. Chemical Reviews 27. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Stereoselective Cyclopropanation Reactions. 2003, 103(4), 977-1050. 28. Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Heterocycles from Alkylidenecyclopropanes. 2003, 103(4), 1213-69. 29. Komatsu, K.; Kitagawa, T. Cyclopropenylium Cations, Cyclopropenones, and Heteroanalogues-Recent Advances. 2003, 103(4), 1371-427. 30. Lee-Ruff, E.; Mladenova, G. Enantiomerically Pure Cyclobutane Derivatives and Their Use in Organic Synthesis. 2003, 103(4), 1449-83. 31. Namyslo, J. C.; Kaufmann, D. E. The Application of Cyclobutane Derivatives in Organic Synthesis. 2003, 103(4), 1485-537. 32. Sadana, A. K.; Saini, R. K.; Billups, W. E. Cyclobutarenes and Related Compounds. 2003, 103(4), 1539602. 33. Gnad, F.; Reiser, O. Synthesis and Applications of β-Aminocarboxylic Acids Containing a Cyclopropane Ring. 2003, 103(4), 1603-23. 34. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds. 2003, 103(4), 1625-47. 35. van der Boom, M. E.; Milstein, D. Cyclometalated Phosphine-Based Pincer Complexes: Mechanistic Insight in Catalysis, Coordination, and Bond Activation. 2003, 103(5), 1759-92. 7930 J. Org. Chem., Vol. 68, No. 20, 2003
36. Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. PalladiumAssisted Routes to Nucleosides. 2003, 103(5), 1875-916. 37. Chen, X.; Fan, Y.; Zheng, Y.; Shen, Y. Properties and Production of Valienamine and Its Related Analogues. 2003, 103(5), 1955-77. 38. Negishi, E.-I.; Anastasia, L. Palladium-Catalyzed Alkynylation. 2003, 103(5), 1979-2017. 39. Biellmann, J.-F. Enantiomeric Steroids: Synthesis, Physical, and Biological Properties. 2003, 103(5), 201933. 40. Fleming, F. F.; Wang, Q. Unsaturated Nitriles: Conjugate Additions of Carbon Nucleophiles to a Recalcitrant Class of Acceptors. 2003, 103(5), 2035-77. 41. Roesky, H. W.; Haiduc, I.; Hosmane, N. S. Organometallic Oxides of Main Group and Transition Elements Downsizing Inorganic Solids to Small Molecular Fragments. 2003, 103(7), 2579-95. 42. Spiegel, D. A.; Njardarson, J. T.; McDonald, I. M.; Wood, J. L. The Art of Innovation in Organic Chemistry: Synthetic Efforts Toward the Phomoidrides. 2003, 103(7), 2691-727. Chemical Society Reviews 43. Fischer, I. Time-Resolved Photoionization of Radicals, Clusters and Biomolecules: Relevant Model Systems. 2003, 32(2), 59-69. 44. Pohlki, F.; Doye, S. The Catalytic Hydroamination of Alkynes. 2003, 32(2), 104-14. ChemistrysA European Journal 45. Corminboeuf, O.; Quaranta, L.; Renaud, P.; Liu, M.; Jasperse, C. P.; Sibi, M. P. Chiral Relay: A Novel Strategy for the Control and Amplification of Enantioselectivity in Chiral Lewis Acid Promoted Reactions. 2003, 9(1), 28-35. 46. Ikunaka, M. A Process in Need is a Process Indeed: Scalable Enantioselective Synthesis of Chiral Compounds for the Pharmaceutical Industry. 2003, 9(2), 378-88. 47. Alcaide, B.; Almendros, P. Non-Metathetic Behavior Patterns of Grubbs' Carbene. 2003, 9(6), 1258-62. Chemistry of Heterocyclic Compounds 48. Voitenko, Z. V.; Egorova, T. V.; Kovtunenko, V. A. Triazolo- and Tetrazoloisoindoles. (Review). 2002, 38(9), 1019-39. 49. Belostotskaya, I. S.; Vol’eva, V. B.; Komissarova, N. L. Heterocycles Based on Sterically Hindered Phenols and Their Derivatives. 2002, 38(10), 1159-73. 50. Kisel, V. M.; Kostyrko, E. O.; Kovtunenko, V. A. Synthesis and Biological Properties of Isoquinolines Spirofused with Carbocycles and Heterocycles at Position 4. (Review). 2002, 38(11), 1295-318. CHEMTRACTS: Organic Chemistry 51. Donghi, M.; Habermann, J.; Ley, S. V. Benzotriazoles in Solid-Phase Organic Chemistry. 2002, 15(14), 751-65. 52. Li, C.-J.; Wang, D. Organic Synthesis via CarbonCarbon Bond Formation in Water. 2003, 16(2), 59-78.
53. Kellogg, R. M. Recent Developments in the Use of Gallium Halides in Organic Synthesis. 2003, 16(2), 7992. 54. Kresge, A. J. Photochemical Generation and Absolute Reactivity of an Allene Oxide in Solution. 2003, 16(2), 93-6. 55. Blackman, B.; Georg, G. I. Stereoselective Syntheses of Epothilones A and B via Nitrile Oxide Cycloadditions. 2003, 16(2), 97-104. 56. Judd, W. R.; Aube, J. Total Syntheses of Martinella Alkaloids. 2003, 16(2), 105-16. Chirality 57. Katagiri, T.; Uneyama, K. Stereospecific Substitution at R-Carbon to Trifluoromethyl Group: Application to Optically Active Fluorinated Amino Acid Syntheses. 2003, 15(1), 4-9. 58. Wenzel, T. J.; Wilcox, J. D. Chiral Reagents for the Determination of Enantiomeric Excess and Absolute Configuration Using NMR Spectroscopy. 2003, 15(3), 256-70. 59. Akita, H.; Nakamura, H.; Ono, M. Total Synthesis of (+)-Macrosphelides A, C, E, F, and G Based on Enzymatic Function. 2003, 15(4), 352-9. 60. Allenmark, S. Induced Circular Dichroism by Chiral Molecular Interaction. 2003, 15(5), 409-22. Coordination Chemistry Reviews 61. Sarkar, B.; Mukhopadhyay, P.; Bharadwaj, P. K. Laterally Non-Symmetric Aza-Cryptands: Synthesis, Catalysis and Derivatization to New Receptors. 2003, 236(1-2), 1-13. 62. Bertani, R.; Casarin, M.; Pandolfo, L. The Organometallic Chemistry of Ph3P:C:C:O. A Route to MetalSubstituted Ketenes. 2003, 236(1-2), 15-33. 63. Ligtenbarg, A. G. J.; Hage, R.; Feringa, B. L. Catalytic Oxidations by Vanadium Complexes. 2003, 237(1-2), 89-101. 64. Bolm, C. Vanadium-Catalyzed Asymmetric Oxidations. 2003, 237(1-2), 245-56. 65. Pratap Reddy, P.; Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Recent Advances in the Oxovanadium Mediated Biaryl Coupling and Modified Mannich-Type Reactions. 2003, 237(1-2), 257-69. Current Medicinal Chemistry 66. Pinto, M. M. M.; Sousa, E. P. Natural and Synthetic Xanthonolignoids: Chemistry and Biological Activities. 2003, 10(1), 1-12. 67. Baltina, L. A. Chemical Modification of Glycyrrhizic Acid as a Route to New Bioactive Compounds for Medicine. 2003, 10(2), 155-71. Current Organic Chemistry 68. Zamojski, A.; Jarosz, S. Iron Complexes in Carbohydrate Chemistry. 2003, 7(1), 1-12. 69. RajanBabu, T. V.; Casalnuovo, A. L.; Ayers, T. A.; Nomura, N.; Jin, J.; Park, H.; Nandi, M. Ligand Tuning as a Tool for the Discovery of New Catalytic Asymmetric Processes. 2003, 7(4), 301-16.
70. Kazmaier, U. Palladium Catalyzed Allylic Alkylations of Nonstabilized Enolates. 2003, 7(4), 317-28. 71. Herndon, J. W. Design of New Reaction Processes Based on Cyclopropylcarbene-Metal Complexes. 2003, 7(4), 329-52. 72. Tanaka, M.; Sakai, K.; Suemune, H. Asymmetric Rhodium-Catalyzed Intramolecular Hydroacylation for Five-Membered Ring Ketone Formation. 2003, 7(4), 35367. 73. Takacs, J. M.; Jiang, X.-t. The Wacker Reaction and Related Alkene Oxidation Reactions. 2003, 7(4), 369-96. 74. Gallos, J. K.; Koumbis, A. E. 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates. 2003, 7(5), 397-425. 75. Purwanto, M. G. M.; Weisz, K. Non-Natural Nucleosides for the Specific Recognition of Watson-Crick Base Pairs. 2003, 7(5), 427-46. 76. Li, L.-S.; Wu, Y.-L. Recent Progress in Syntheses of Higher 3-Deoxy-2-Ulosonic Acids and Their Derivatives. 2003, 7(5), 447-75. 77. Baillie, C.; Xiao, J. Catalytic Synthesis of Phosphines and Related Compounds. 2003, 7(5), 477-514. 78. Tai, D.-F. Enzymatic Peptide Synthesis: From the Substrate Point of View. 2003, 7(6), 515-54. 79. Lee, A. W. M.; Chan, W. H.; Zhang, H. K.; Xia, P. F. Sulfonate and Sulfonamide Activated Olefins and Acetylenes in [4+2] Cycloaddition Reactions. 2003, 7(6), 573-83. 80. Koumbis, A. E.; Gallos, J. K. 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 2: Nitrones and Oximes. 2003, 7(6), 585-628. 81. Gros, P.; Fort, Y. Modern Synthetic Methods for Preparation of N-Containing Bisheteroaromatic Compounds. 2003, 7(7), 629-48. 82. Witt, A.; Bergman, J. Recent Developments in the Field of Quinazoline Chemistry. 2003, 7(7), 659-77. 83. Hadjeri, M.; Beney, C.; Boumendjel, A. Recent Advances in the Synthesis of Conveniently Substituted Flavones, Quinolones, Chalcones and Aurones: Potential Biologically Active Molecules. 2003, 7(7), 679-89. 84. Shi, M.; Shen, Y.-M. Recent Progress in the Fixation of Carbon Dioxide. 2003, 7(8), 737-45. 85. Rossi, R. A.; Postigo, A. Recent Advances in Radical Nucleophilic Substitution Reactions. 2003, 7(8), 747-69. 86. Koumbis, A. E.; Gallos, J. K. 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 3: Azides, Diazo Compounds and Other Dipoles. 2003, 7(8), 771-97. 87. Khlestkin, V. K.; Mazhukin, D. G. Recent Advances in the Application of N,O-Dialkylhydroxylamines in Organic Chemistry. 2003, 7(10), 967-93. Heterocycles 88. Reddy, P. S.; Reddy, P. P.; Vasantha, T. A Review on 2-Heteryl and Heteroalkyl-4(3H)-Quinazolinones. 2003, 60(1), 183-226. 89. Ryzhakov, A. V.; Andreev, V. P.; Rodina, L. L. Molecular Complexes of Heteroaromatic N-Oxides and Their Reactions with Nucleophiles. 2003, 60(2), 419-35. 90. Kashima, C. Synthetic Utility of N-Acylpyrazoles. 2003, 60(2), 437-55. J. Org. Chem, Vol. 68, No. 20, 2003 7931
91. Lukevics, E.; Arsenyan, P.; Pudova, O. Methods for the Synthesis of Oligothiophenes. 2003, 60(3), 663-87. 92. Kashima, C. 3-Phenyl-l-menthopyrazole [(4R,7S)7-Isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydroindazole]: A New Type of Chiral Auxiliary. 2003, 60(4), 95987. Natural Product Reports 93. Mander, L. N. Twenty Years of Gibberellin Research. 2003, 20(1), 49-69. 94. Somei, M.; Yamada, F. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. 2003, 20(2), 216-42.
Faber, K. Biomimetic Approach to the Stereoselective Synthesis of Acetogenins. 2003, 75(2-3), 259-64. 109. Gasparrini, F.; D’Acquarica, I.; Misiti, D.; Pierini, M.; Villani, C. Natural and Totally Synthetic Receptors in the Innovative Design of HPLC Chiral Stationary Phases. 2003, 75(2-3), 407-12. 110. Feringa, B. L.; van Delden, R. A.; ter Wiel, M. K. J. In Control of Switching, Motion, and Organization. 2003, 75(5), 563-75. 111. Juaristi, E.; Rosquete-Pina, G. A.; VazquezHernandez, M.; Mota, A. J. Salt Effects on the Conformational Behavior of 5-Substituted 1,3-Dioxanes. 2003, 75(5), 589-99. Russian Chemical Reviews
Organic Preparations and Procedures International 95. Spino, C. Chiral Enolate Equivalents. A Review. 2003, 35(1), 1-140. 96. Gelmi, M. L.; Pocar, D. Heterosubstituted Carbocyclic R-Amino Acids. A Review. 2003, 35(2), 141-205. Pure and Applied Chemistry 97. Pushpan, S. K.; Chandrashekar, T. K. Aromatic Core-Modified Expanded Porphyrinoids with Meso-Aryl Substituents. 2002, 74(11), 2045-55. 98. Ernst, H. Recent Advances in Industrial Carotenoid Synthesis. 2002, 74(11), 2213-26. 99. Glueck, S. M.; Mayer, S. F.; Kroutil, W.; Faber, K. Advances in Biocatalytic Synthesis. Enzyme-Triggered Asymmetric Cascade Reactions. 2002, 74(12), 2253-7. 100. Narasaka, K. Synthesis of Azaheterocycles from Oxime Derivatives. 2003, 75(1), 19-28. 101. Ellman, J. A. Applications of tert-Butanesulfinamide in the Asymmetric Synthesis of Amines. 2003, 75(1), 39-46. 102. Padwa, A. Application of Cascade Processes Toward Heterocyclic Synthesis. 2003, 75(1), 47-62. 103. Hofle, G.; Glaser, N.; Leibold, T.; Karama, U.; Sasse, F.; Steinmetz, H. Semisynthesis and Degradation of the Tubulin Inhibitors Epothilone and Tubulysin. 2003, 75(2-3), 167-78. 104. Wong, C.-H.; Bryan, M. C.; Nyffeler, P. T.; Liu, H.; Chapman, E. Synthesis of Carbohydrate-Based Antibiotics. 2003, 75(2-3), 179-86. 105. Banwell, M. G.; Edwards, A. J.; Harfoot, G. J.; Jolliffe, K. A.; McLeod, M. D.; McRae, K. J.; Stewart, S. G.; Vogtle, M. Chemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors. 2003, 75(2-3), 223-9. 106. Picoul, W.; Bedel, O.; Haudrechy, A.; Langlois, Y. Progress in Fumagillin Synthesis. 2003, 75(2-3), 23549. 107. Nishikawa, T.; Urabe, D.; Yoshida, K.; Iwabuchi, T.; Asai, M.; Isobe, M. Total Syntheses of 11-Deoxytetrodotoxin and 8,11-Dideoxytetrodotoxin. 2003, 75(2-3), 251-7. 108. Orru, R. V. A.; Groenendaal, B.; van Heyst, J.; Hunting, M.; Wesseling, C.; Schmitz, R. F.; Mayer, S. F.; 7932 J. Org. Chem., Vol. 68, No. 20, 2003
112. Shevchenko, V. P.; Nagaev, I. Y.; Myasoedov, N. F. Solid-Phase Method for Tritium Labelling of Biologically Active Compounds. 2003, 72(5), 423-46. 113. Pozharskii, A. F. Naphthaldehydes. 2003, 72(5), 447-70. Science 114. Kochendoerfer, G. G.; Chen, S.-Y.; Mao, F.; Cressman, S.; Traviglia, S.; Shao, H.; Hunter, C. L.; Low, D. W.; Cagle, E. N.; Carnevali, M.; Gueriguian, V.; Keogh, P. J.; Porter, H.; Stratton, S. M.; Wiedeke, M. C.; Wilken, J.; Tang, J.; Levy, J. J.; Miranda, L. P.; Crnogorac, M. M.; Kalbag, S.; Botti, P.; Schindler-Horvat, J.; Savatski, L.; Adamson, J. W.; Kung, A.; Kent, S. B. H.; Bradburne, J. A. Design and Chemical Synthesis of a Homogeneous Polymer-Modified Erythropoiesis Protein. 2003, 299(5608), 884-7. 115. Ammal, S. C.; Yamataka, H.; Aida, M.; Dupuis, M. Dynamics-Driven Reaction Pathway in an Intramolecular Rearrangement. 2003, 299(5612), 1555-7. 116. Lin, J. J.; Zhou, J.; Shiu, W.; Liu, K. State-Specific Correlation of Coincident Product Pairs in the F + CD4 Reaction. 2003, 300(5621), 966-9. Sulfur Reports 117. Sadekov, I. D.; Zakharov, A. V.; Maksimenko, A. A. Diorganyl Derivatives of Tellurium(IV) (σ-Telluranes of R2TeX2 Type). 2002, 23(2), 125-207. 118. Okuma, K. Recent Studies on the Reactions of Thioaldehydes and Thioketones. 2002, 23(2), 209-41. 119. Siegemund, A.; Taubert, K.; Schulze, B. 1,2Benzisothiazol-3(2H)-ones and Heterocyclic Annelated Isothiazol-3(2H)-ones, Part II: Synthesis, Reactions, and Biological Activity. 2002, 23(3), 279-319. 120. Voronkov, M.; Deryagina, E. Thermal Transformations of Organic Compounds of Tetra- and Hexavalent Sulfur. 2002, 23(3), 321-87. Synlett 121. Miura, K.; Hosomi, A. Stereoselective Synthesis of Substituted Cyclic Ethers and Amines by AcidCatalyzed Cyclization of Vinylsilanes Bearing a Hydroxy or Amino Group. 2003, (2), 143-55. 122. Nair, V.; Panicker, S. B.; Nair, L. G.; George, T. G.; Augustine, A. Carbon-Heteroatom Bond-Forming
Reactions Mediated by Cerium(IV) Ammonium Nitrate: An Overview. 2003, (2), 156-65. 123. Katsuki, T. Some Recent Advances in Metallosalen Chemistry. 2003, (3), 281-97. 124. Catellani, M. Catalytic Multistep Reactions via Palladacycles. 2003, (3), 298-313. 125. Anon. NHC Ruthenium Complexes as Second Generation Grubbs Catalysts. 2003, (3), 423-4. 126. Griesbeck, A. G. Spin-Selectivity in Photochemistry: A Tool for Organic Synthesis. 2003, (4), 451-72. 127. Anon. Pyrrolidine-2-carboxylic Acid (L-Proline). 2003, (4), 582-3. 128. Krauss, R.; Koert, U. Molecular Signal Transduction by Conformational Transmission. 2003, (5), 598-608. SynthesissStuttgart 129. Fallahpour, R.-A. Synthesis of 4′-Substituted 2,2′: 6′,2′′-Terpyridines. 2003, (2), 155-84. 130. Langlois, B. R.; Billard, T. Some Recent Results in Nucleophilic Trifluoromethylation and Introduction of Fluorinated Moieties. 2003, (2), 185-94. 131. Podlech, J.; Maier, T. C. Indium in Organic Synthesis. 2003, (5), 633-55. 132. Rheault, T. R.; Sibi, M. P. Radical-Mediated Annulation Reactions. 2003, (6), 803-19. Tetrahedron 133. Sandford, G. Perfluoroalkanes. 2003, 59(4), 43754.
134. Dembitsky, V. M.; Srebnik, M. Synthesis and Biological Activity of R-Aminoboronic Acids, AmineCarboxyboranes and Their Derivatives. 2003, 59(5), 57993. 135. Pellissier, H.; Santelli, M. The Use of Arynes in Organic Synthesis. 2003, 59(6), 701-30. 136. Brase, S.; Kirchhoff, J. H.; Kobberling, J. Palladium-Catalyzed Reactions in Solid-Phase Organic Synthesis. 2003, 59(7), 885-939. 137. Mander, L. N.; Williams, C. M. Oxidative Degradation of Benzene Rings. 2003, 59(8), 1105-36. 138. Rezgui, F.; Amri, H.; El Gaied, M. M. Synthetic Methods for R-Substituted Cyclic R,β-Enones. 2003, 59(9), 1369-80. 139. Singleton, J. T. The Uses of Pincer Complexes in Organic Synthesis. 2003, 59(11), 1837-57. 140. Alexander, C.; Davidson, L.; Hayes, W. Imprinted Polymers: Artificial Molecular Recognition Materials with Applications in Synthesis and Catalysis. 2003, 59(12), 2025-57. 141. Harmata, M.; Rashatasakhon, P. Cycloaddition Reactions of Vinyl Oxocarbenium Ions. 2003, 59(14), 2371-95. Tetrahedron: Asymmetry 142. North, M. Synthesis and Applications of NonRacemic Cyanohydrins. 2003, 14(2), 147-76. 143. Perry, M. C.; Burgess, K. Chiral N-Heterocyclic Carbene-Transition Metal Complexes in Asymmetric Catalysis. 2003, 14(8), 951-61.
Contributed Volumes Progress in Heterocyclic Chemistry. Volume 15. Gribble, G., Joule, J., Eds., Elsevier: Oxford, U.K., 2003. 144. Walters, M. A. Recent Advances in the Synthesis of Heterocycles via Ring-Closing Metathesis. 145. Pavl, J. W. Photochemical Isomerizations of Some Five-Membered Heteroaromatic Azoles. 146. Gribble, G. W. Naturally Occurring Halogenated Pyrroles and Indoles. Targets in Heterocyclic SystemssChemistry and Properties. Volume 6. Attanasi, O. A., Spinelli, D., Eds., Italian Society of Chemistry: Rome, Italy, 2002. 147. Cossy, J.; Pardo, D. G. Enantioselective Ring Expansion via Aziridinium Intermediates. Synthesis of Substituted Piperidines from Substituted Pyrrolidines. Synthetic Applications. 148. Tagliatesta, P. The Formation of the CarbonCarbon Bond Catalyzed by Metalloporphyrins. 149. Elguero, J.; Goya, P.; Jagerovic, N.; Silva, A. M. S. Pyrazoles as Drugs: Facts and Fantasies. 150. Petrini, M. Recent Advances in the Synthesis of Saturated Nitrogen Heterocycles Using N-Acyliminium Ion Intermediates.
151. Yus, M.; Foubelo, F. Reductive Opening of Heterocycles with Lithium Metal as a Source of Functionalised Organolithium Compounds: Synthetic Applications. 152. Kollenz, G.; Leber, S. Furan-2,3-diones: Convenient Synthons in Heterocyclic Chemistry. 153. Vasapollo, G.; Mele, G. Metal-Catalyzed Cyclocarbonylation Reactions for the Synthesis of Lactones and Lactams. 154. Avenoza, A.; Busto, J. H.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Sucunza, D.; Zurbano, M. M. Preparation and Synthetic Applications of (S)- and (R)N-BOC-N,O-Isopropylidene-methylserinals. 155. Keglevich, G. Synthesis and Reactivity of 1-(2,4,6Trialkylphenyl)Phospholes with a Flattened P-Pyramid. 156. Anakabe, E.; Badı´a, D.; Carrillo, L.; Reyes, E.; Vicario, J. L. Chiral Aminoalcohols and Derivatives in the Asymmetric Synthesis of the Tetrahydroisoquinolines. 157. Greck, C.; Poupardin, O. Stereoselective Synthesis of Nitrogen Heterocycles of Enantiopure 3-Hydroxy Esters through Electrophilic Amination. 158. Elgemeie, G. H.; Abd-Elaziz, G. W. Recent Trends in the Synthesis of Heterocycles using Ketene-Dithioacetals with Electron Attracting Groups. J. Org. Chem, Vol. 68, No. 20, 2003 7933
159. Tapolcsa´nyi, P.; Ma´tyus, P. Recent Development in the Chemistry of 4,5-Dihalo-3(2H)-Pyridazinones. 160. Hatem, J. Synthesis of Heterocycles from Allenes by Intramolucular Ring Closure. The Alkaloids. Volume 58. Cordell, G., Ed., Academic Press: San Diego, 2002. 161. Bienz, S.; Detterbeck, R.; Ensch, C.; Guggisberg, A.; Hausermann, U.; Meisterhans, C.; Wendt, B.; Werner, C.; Hesse, M. Putrescine, Spermidine, Spermine, and Related Polyamine Alkaloids. 162. Rathbone, D. A. et al. Biotransformation of Alkaloids. The Porphyrin Handbook: Volumes 11-20. Kadish, K. M., Smith, K. M., Guiland, R., Eds., Academic Press: San Diego, 2003.
163. Volume 11. Bioinorganic and Bioorganic Chemistry. 164. Volume 12.The Iron and Cobalt Pigments: Biosynthesis, Structure, and Degradation. 165. Volume 13. Chlorophylls and Bilins: Biosynthesis, Synthesis, and Degradation. 166. Volume 14. Medical Aspects of Porphyrins. 167. Volume 15. Phthalocyanines: Synthesis. 168. Volume 16. Phthalocyanines: Spectroscopic and Electrochemical Characterization. 169. Volume 17. Phthalocyanines: Properties and Materials. 170. Volume 18. Multiporphyrins, Multiphthalocyanines, and Arrays. 171. Volume 19. Applications of Phthalocyanines 172. Volume 20. Phthalocyanines: Structural Characterization.
Monographs 173. Fleming, I., Ed. Science of Synthesis, Volume 4, Houben-Weyl Methods of Molecular Transformations; Organometallics: Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds. Georg Thieme Verlag: Stuttgart, Germany, 2002. 174. Gielen, M., Willem, R., Wrackmeyer, B., Eds. Unusual Structures and Physical Properties in Organometallic Chemistry. [In: Phys. Organomet. Chem., 2002; 3]. John Wiley & Sons Ltd.: Chichester, U.K., 2002. 175. Lautens, M., Ed. Science of Synthesis, Volume 1, Houben-Weyl Methods of Molecular Transformations; Organometallics: Compounds with Transition MetalCarbon π-Bonds and Compounds of Groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os). Georg Thieme Verlag: Stuttgart, Germany, 2002.
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176. Link, J. T., Hanson, R. M., Eds. Organic Reactions (New York). Volume 60. John Wiley & Sons: Hoboken, NJ, 2002. 177. Marek, I. Titanium and Zirconium in Organic Synthesis. Wiley-VCH Verlag: Weinheim, Germany, 2002. 178. Nicolaou, K. C.; Hanko, R.; Hartwig, W. Handbook of Combinatorial Chemistry, Volume 1: Drugs, Catalysts, Materials. Wiley-VCH Verlag: Weinheim, Germany, 2002. 179. Nicolaou, K. C.; Hanko, R.; Hartwig, W. Handbook of Combinatorial Chemistry, Volume 2: Drugs, Catalysts, Materials. Wiley-VCH Verlag: Weinheim, Germany, 2002. 180. Roesky, H. W.; Atwood, D. A.; Eds. Group 13 Chemistry I: Fundamental New Developments. [In: Struct. Bonding (Berlin, Germany), 2002; 103]. SpringerVerlag: Berlin, Germany, 2002.
Index Acetogenins, stereoselective synthesis, 108 Acetylenes, cycloaddition, electron-withdrawing activator, 79 Acyliminium ion intermediates, book, 150 Acyliminium, cascade processes, 102 Acylpyrazoles, 90 Aldehydes, asymmetric amination, 20 Alkaloids, Martinella, synthesis, 56 polyamine, book, 161 polyhydroxylated, synthesis, 80 putrescine, book, 161 quinazoline, 82 spermidine, book, 161 spermine, book, 161 transformations, book, 162 Alkenes, Wacker oxidation, 73 Alkyl group, cross coupling, functional group tolerant, 17 Alkylboranes, cross coupling review, 17 Alkylidenecyclopropanes, cycloaddition, 28 Alkylzinc, cross coupling, 17 Alkynes, hydroamination, 44 Alkynylation, Pd catalyst, 38 Allene oxides, photochemical generation, 54 Amides, phenylsulfinylmethyl, cascade processes, 102 Amines, asymmetric synthesis, 101 cyclic, stereoselective synthesis, 121 molecular recognition, 23 preparation, using propanesulfinamide, 101 via tertbutyl sulfinamide, 101 Amino acid, stereospecific fluorination, 57 heterosubstituted, carbocyclic, 96 Aminoalcohols, chiral, in synthesis, book, 156 Aminoboronic acid, R-, 134 Aminocarboxy boranes, 134 Aminocarboxylic acids, with cyclopropane ring, 33 Annulation, radical mediated, 132 Antibacterial agents, valienamine, 37 Antibiotics, carbohydrate-based, 104 Arenes, electrophilic substitution, 19 Aromatics, electrophilic substitution, 19 Arynes, in synthesis, 135 Asymmetric catalysis, 9 Asymmetric oxidation, vanadium catalyst, 64 Asymmetric synthesis, 46 Aurones, preparation, 83 Aza-cryptands, 61 Azaflavones, preparation, 83 Aza-Henry reaction, 16 Azaheterocycles, from oximes, 100 isoquinoline, preparation, 100 N-containing, preparation, 100 pyridine, preparation, 100 pyrrole, preparation, 100 spiro imine, preparation, 100 Azides, 1,3-dipolar cycloaddition, 80 dipolar cycloaddition, 86 Aziridinium intermediates, book, 147 Azodicarboxylates, 20
Azoles, heteroaromatic, photochemical isomerization, 145 Azomethine, 86 Benzene, oxidative degradation, 137 ring cleavage, 137 Benzisothiazolones, 119 Benzocyclobutenes, 32 Benzotriazoles, solid-phase synthesis, 51 BINAP catalyst, 9 Biomimetics, acetogenins, 108 Bromination, with vanadium bromoperoxidase, 63 Carbene rearrangement, solid state, 2 Carbenes, chiral N-heterocyclic, complex, 143 triplet, 24 Carbocycles, eight membered, via Rh catalysis, 18 Carbohydrates, aminoglycosides, 104 antibiotics, 104 enzymic synthesis, 25 iron complexes, 68 mimics, 74, 80, 86 Carbon dioxide fixation, 84 Carbon heteroatom bond formation, 122 Carboranes, super-, 22 Carotenoids, industrial synthesis, 98 Cascade reactions, enzyme triggered, 99 heterocyclic synthesis, 102 Catalysis, ligand tuning, 69 Catalysts, cerium ammonium nitrate, 122 N-heterocyclic carbene complex, 143 C-C bond formation, water solvent, 52 Chalcones, substituted, 83 Chiral compounds, enantioselctive synthesis, 46 Chiral pool, 46 Chiral reagents, enantiomeric excess, NMR, 58 Chlorophyll, book, 165 Circular dichroism, chiral molecule induced, 60 Coincident product pairs, 116 Combinatorial chemistry, catalysts, book, 178-9 drugs, book, 178-9 with Pd, 136 Cucurbituril homologs, 6 Cyanohydrins, catalytic asymmetric synthesis, 142 Cyclic enones, preparation, 138 Cycloaddition, of vinyl oxocarbenium ion, 141 sulfonamide activator, 79 sulfonate activator, 79 Cyclobutanes, enantiomerically pure, 30 in synthesis, 31 ring opening, 31 Cyclobutarenes, 32 Cyclocarbonylation, book, 153 Cyclooligothiophenes, preparation, 91 Cyclopentanone derivatives, preparation, 72 Cycloproanation, stereoselective, 27 Cyclopropanes, biosynthesis, 34 in aminocarboxylic acids, 33 Cyclopropenones, 29 Cyclopropenylium cations, 29
Cyclopropylcarbene metal complex, reactions, 71 Deoxytetrodotoxin, preparation, 107 Desymmetrization, 46 Dialkylhydroxylamines, 87 Diamines, asymmetric preparation, 16 Diaminocarboxylic acid, asymmetric preparation, 16 Dideoxytetrodotoxin, preparation, 107 Diels-Alder reaction, cascade process, 102 electron withdrawing activator, 79 Dihalopyridazinones, 159 Diorganotellurium, 117 Dioxanes, conformations, salt effect, 111 Diphosphine chirogenic ligands, 12 Domino reactions, enzyme triggered, 99 heterocyclic synthesis, 102 Dynamics, reaction pathway, 115 Enantiomeric resolution, HPLC, 109 Enolates, allylic alkylation, 70 chiral, equivalents, 95 Enones, cyclic, preparation, 138 Epothilone, tubulin inhibitor, 103 stereoselective synthesis, 55 via nitrile oxide cycloaddition, 55 Erythropoiesis protein, polymer modified, 114 Ethers, cyclic, stereoselective synthesis, 121 Flavones, substituted, 83 Fluorination, 130 Fumagillin, preparation, 106 Furan-2,3-diones, book, 152 Gallium trichloride, in synthesis, 53 Gibberellins, synthesis, 93 Gigantrionenin, stereoselective synthesis, 108 Glycocalixarene, 1 Glycyrrhizic acid, chemical modification, 67 Grubbs carbene, catalytic activity, 47 Grubbs catalyst, preparation, 125 Haloalkanes, cross coupling, 17 Halogenation catalyst, 63 Heme proteins, electron tunneling, book, 163 Heteroaromatics, N-oxide molecular complexes, 89 Heterocycles, benzoquinone, 49 from alkylidenecyclopropanes, 28 from allenes, book, 160 hindered phenol, 49 N-containing, book, 150 N-containing, book, 157 ring opening, lithium, book, 151 synthesis, cascade reactions, 102 via intramolecular ring closure, 160 via ketene-dithioacetals, 158 via ring-closing metathesis, book, 144 Heterocyclic carbene ruthenium complexes, 125 Host-guest compounds, physicochemistry, 7 covalent coupling, 23 Houben-Weyl transformations, book, 173, 175
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HPLC enantioselective stationary phase, 109 Hydrazino carbonyls, synthesis, 20 Hydroboration, via borane amine complexes, 15 Hydrocyanation, 69 Hydrogenation, 69 asymmetric, 8, 12, 13 enantioselective, 10,11 fine chemical preparation, 13 Hydrogenolysis, 112 Hydroxy esters, electrophilic amination, book, 157 Hydroxytetradecanoic acid, preparation, 46 Indazoles, isopropylmethyltetrahydro, 92 Indium, in organic synthesis, 131 Indole alkaloids, nonrearranged, 94 Indoles, halogenated, natural, 146 Isopropylidenemethylserinals, book, 154 Isopropylmethyltetrahydroindazole, 92 Isoquinolines, spiro, with carbocycles, 50 spiro, with heterocycles, 50 spirocyclization, 50 Isothiazolones, heterocyclic, annelated, 119 Ketenes, metal substituted, synthesis, 62 Ketenylidenetriphenylphosphoranes, 62 Ketones, R,β-unsaturated, epoxidation, 14 asymmetric amination, 20 Kinetic effects, reaction pathway, 115 Lactams, via cyclocarbonylation, book, 153 Lactones, via cyclocarbonylation, book, 153 Lewis acids, amplified enantioselectivity, 45 chiral relay, 45 Ligands, pincer complexes, 139 Macrosphelides preparation, 59 Mannich reaction, with oxovanadium, 65 Menthopyrazoles, phenyl, preparation, 92 Meso compounds, stereoselective synthesis, 21 Metallophthalocyanines, book, 168, 171 Metalloporphyrins, book, 148, 168 chiral, book, 163 Metallosalen ligands, catalysts, 123 Microchannel reactor, enzymic synthesis, 25 Molecular recognition, artificial, 140 imprinted polymer, 140 Molecular switch, chiroptical, 110 Monoterpenoids, 94 Nanotubes, binding activity, 1 Naphthaldehydes, 113 Naphthalenes, formylation, 113 Nitrile oxides, dipolar cycloaddition, 74 Nitriles, unsaturated, addition to C nucleophiles, 40 Nitronates, dipolar cycloaddition, 74 Nitrones, 1,3-dipolar cycloadditions, 80 Nucleoside analogs, DNA base pair recognition, 75
via azide dipolar cycloaddition, 86 Nucleosides, Pd cross-coupling, 36 preparation, 80 Olefin metathesis, catalyst, 125 Olefins, cycloaddition, electron-withdrawing activator, 79 enantioselective hydrogenation, 10 Oligothiophenes, preparation, 91 Organolithium, synthesis, book, 151 Organometallic oxides, 41 Organometallics, group 13, book, 180 group 15, book, 173 unusual, book, 174 Organosilicon compounds, book, 173 Organosulfur, hexavalent, thermal transformation, 120 tetravalent, thermal transformation, 120 Oxidation catalyst, 63 Oxovanadium biaryl coupling, 65 Palladacycles, multistep catalytic reaction, 124 regiochemistry, 124 Palladium, in solid-phase synthesis, 136 Peptides, synthesis, enzymic, 78 Peptidocalixarene, 1 Perfluoroalkanes, 133 Phenylbutenylpentalenepentanoic acid, 9 Phenylmenthopyrazoles, 92 Phomoidrides, 42 Phosphines, preparation, 77 Photochemistry, spin selectivity, 126 Photoionization, biomolecules, time-resolved, 43 Pincer complex, 139 cyclometalated phosphine, 35 Piperidines, from pyrrolidines, book, 147 Polyheteroaromatics, N containing, preparation, 81 preparation, 81 Polymers, imprinted, catalysis, 140 Porphyrinoids, heptaphyrin, 97 hexaphyrin, 97 meso aryl substituents, 97 octaphyrin, 97 rubyrin, 97 sapphyrin, 97 smaragdyrin, 97 Porphyrins, bilins, book, 165 bioorganic, book, 163 chlorophylls, book, 165 drugs, book, 166 iron cobalt pigments, book, 164 multiphthalocyanine, book, 170 multiporphyrins, book, 170 phthalocyanine, book, 167-72 Proline, synthesis, 127 Pummerer reaction, cascade process, 102 Pyrazoles, medicinal use, book, 149 Pyrazolidines, synthesis, 80 Pyrazolines, synthesis, 80 Pyrroles, halogenated, natural, 146 Pyrrolidine-2-carboxylic acid, 127 Quinazolines, 82 Quinazolinones, 82
7936 J. Org. Chem., Vol. 68, No. 20, 2003
heteroalkyl, 88 heterocyclic, 88 Quinolones, substituted, 83 Radicals, nucleophilic substitution, 85 photoionization, 43 Reactions, book, 176 Ruthenium, heterocyclic carbene complexes, 125 Sesquiterpenoids, chemoenzymic preparation, 105 enantioselective preparation, 105 Signal transduction, by conformational transmission, 128 Solid-phase synthesis, using Pd, 136 Stereoselectivity, frictional imposition, 4 Steroids, enantiomeric, 39 Stimulants, spiro-isoquinolines, 50 Supercarboranes, 22 Supramolecular crown ether adducts, gas phase, 23 Supramolecules, cucurbiturils, 6 Synthetic erythropoiesis protein (SEP), 114 Telluranes, 117 Terpyridine ligands, preparation, 129 Tetradeuteriomethane, with monofluorine, 116 Tetrahydroisoquinolines, synthesis, book, 156 Tetrapyrroles, book, 164 Tetrazoloisoindoles, preparation, 48 Thioaldehydes, 118 Thioketones, 118 Titanium, in synthesis, book, 177 Transition metal salen complexes, 123 Transition metal-C π bonds, book, 175 Trialkylphenylphospholes, book, 155 Triazoloisoindoles, preparation, 48 Trifluoromethylation, nucleophilic, 130 Triphenylphosphoranes, ketenylidene-, 62 Tritium labeling, 112 Tubulin inhibitors, 103 Ulosonic acid preparation, 76 Valienamine, preparation, 37 Vanadium-catalyzed asymmetric oxidation, 64 Vanadium compounds, oxidation, 63 Vanadium haloperoxidases, 63 Vibrational effects, reaction pathway, 115 Vinyl oxocarbenium ions, cycloaddition, 141 Vinylic substitution reaction, 5 Vinylsilanes, cyclization, 121 Viscosity tool, stereoselectivity, 4 Vitamin B12, book, 163-4 Wacker oxidation of alkenes, 73 Wittig rearrangement, 26 Xanthones, lignan, synthesis, 66 Xanthonolignoids, Clusiaceae, 66 Zeolites, in asymmetric phororeactions, 3 Zirconium, in synthesis, book, 177 JO033583E
