Number 76 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 latter part of the 2004 literature. Previous installment: J. Org. Chem. 2004, 70(1), 395-404. Supporting Information Available: A file containing this Recent Review compilation in Microsoft Word and the data in plain text that can be imported into Endnote (using Refer style) and Reference Manager databases. 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. Murugavel, R.; Walawalkar, M. G.; Dan, M.; Roesky, H. W.; Rao, C. N. R. Transformations of Molecules and Secondary Building Units to Materials: A Bottom-Up Approach. 2004, 37(10), 763-74. 2. Buergi, T.; Baiker, A. Heterogeneous Enantioselective Hydrogenation over Cinchona Alkaloid Modified Platinum: Mechanistic Insights into a Complex Reaction. 2004, 37(11), 909-17. 3. Mathey, F. Transient 2H-Phospholes as Powerful Synthetic Intermediates in Organophosphorus Chemistry. 2004, 37(12), 954-60. 4. Inoue, M.; Hirama, M. Evolution of a Practical Total Synthesis of Ciguatoxin CTX3C. 2004, 37(12), 9618. 5. Schreiner, P. R.; Navarro-Vazquez, A.; Prall, M. Computational Studies on the Cyclizations of Enediynes, Enyne-Allenes, and Related Polyunsaturated Systems. 2005, 38(1), 29-37. Advanced Synthesis and Catalysis 6. Tohma, H.; Kita, Y. Hypervalent Iodine Reagents for the Oxidation of Alcohols and Their Application to Complex Molecule Synthesis. 2004, 346(2+3), 11124. 7. Kobayashi, S.; Sugiura, M.; Ogawa, C. Neutral Coordinate-Organocatalysts in Organic Synthesis. Allylation of Acylhydrazones with Allyltrichlorosilanes. 2004, 346(9 + 10), 1023-34. 8. Sheldon, R. A.; Arends, I. W. C. E. Organocatalytic Oxidations Mediated by Nitroxyl Radicals. 2004, 346(9 + 10), 1051-71.
9. Luecke, B.; Narayana, K. V.; Martin, A.; Jaehnisch, K. Oxidation and Ammoxidation of Aromatics. 2004, 346(12), 1407-24. 10. Farina, V. Researchers in This Field Still Have Many Challenges in Front of Them, but the Future is Indeed Very Bright. 2004, 346(13-15), 1519-21. 11. Miyaura, N. Heck and Cross-Coupling Reactions: Two Core Chemistries in Metal-Catalyzed Organic Syntheses. 2004, 346(13-15), 1522-3. 12. Netherton, M. R.; Fu, G. C. Nickel-Catalyzed CrossCouplings of Unactivated Alkyl Halides and Pseudohalides with Organometallic Compounds. 2004, 346(1315), 1525-32. 13. Shibasaki, M.; Vogl, E. M.; Ohshima, T. Asymmetric Heck Reaction. 2004, 346(13-15), 1533-52. 14. Farina, V. High-Turnover Palladium Catalysts in Cross-Coupling and Heck Chemistry: A Critical Overview. 2004, 346(13-15), 1553-82. 15. Schlummer, B.; Scholz, U. Palladium-Catalyzed C-N and C-O Coupling-A Practical Guide from an Industrial Vantage Point. 2004, 346(13-15), 1599-626. Angewandte Chemie, International Edition in English 16. Braga, D.; Grepioni, F. Solventless Reactions: Reactions Between or Within Molecular Crystals. 2004, 43(31), 4002-11. 17. North, M. Oxidative Synthesis of R-Amino Nitriles from Tertiary Amines. 2004, 43(32), 4126-8. 18. Kawase, T.; Oda, M. Moebius Aromatic Hydrocarbons: Challenges for Theory and Synthesis. 2004, 43(34), 4396-8.
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19. Ma, J.-A.; Cahard, D. Toward Perfect Catalytic Asymmetric Synthesis: Dual Activation of the Electrophile and the Nucleophile. 2004, 43(35), 4566-83. 20. Chen, Z. Fullerene Derivative: The Smaller Fullerene C50, Isolated as C50Cl10. 2004, 43(36), 4690-1. 21. Espinet, P.; Echavarren, A. M. C-C Coupling: The Mechanisms of the Stille Reaction. 2004, 43(36), 470434. 22. Zanoni, G.; Franzini, M. Elisabethin A: A Marine Diterpenoid Yet to Surrender to Total Synthesis. 2004, 43(37), 4837-41. 23. Li, X.; Liu, D. R. DNA-Templated Organic Synthesis: Nature’s Strategy for Controlling Chemical Reactivity Applied to Synthetic Molecules. 2004, 43(37), 484870. 24. Scott, L. T. Methods for the Chemical Synthesis of Fullerenes. 2004, 43(38), 4994-5007. 25. Nair, V.; Bindu, S.; Sreekumar, V. N-Heterocyclic Carbenes: Reagents, Not Just Ligands! 2004, 43(39), 5130-5. 26. Dalko, P. I.; Moisan, L. In the Golden Age of Organocatalysis. 2004, 43(39), 5138-75. 27. Afonso, C. A. M.; Crespo, J. G. Recent Advances in Chiral Resolution Through Membrane-Based Approaches. 2004, 43(40), 5293-5. 28. Dupont, J.; Spencer, J. On the Noninnocent Nature of 1,3-Dialkylimidazolium Ionic Liquids. 2004, 43(40), 5296-7. 29. Hunter, C. A. Quantifying Intermolecular Interactions: Guidelines for the Molecular Recognition Toolbox. 2004, 43(40), 5310-24. 30. Palomo, C.; Oiarbide, M.; Mielgo, A. Unveiling Reliable Catalysts for the Asymmetric Nitroaldol (Henry) Reaction. 2004, 43(41), 5442-4. 31. Bushey, M. L.; Nguyen, T.-Q.; Zhang, W.; Horoszewski, D.; Nuckolls, C. Using Hydrogen Bonds to Direct the Assembly of Crowded Aromatics. 2004, 43(41), 544653. 32. Koert, U. Syntheses of Tetrodotoxin. 2004, 43(42), 5572-6. 33. Kappe, C. O. Synthetic Methods. Controlled Microwave Heating in Modern Organic Synthesis. 2004, 43(46), 6250-84. Chemical Reviews 34. Knorr, R. Alkylidenecarbenes, Alkylidenecarbenoids, and Competing Species: Which is Responsible for Vinylic Nucleophilic Substitution, [1 + 2] Cycloadditions,1,5-CH Insertions, and the Fritsch-ButtenbergWiechell Rearrangement? 2004, 104(9), 3795-849. 35. Brink, G. J. t.; Arends, I. W. C. E.; Sheldon, R. A. The Baeyer-Villiger Reaction: New Developments Toward Greener Procedures. 2004, 104(9), 4105-23. 36. Langer, P.; Freiberg, W. Cyclization Reactions of Dianions in Organic Synthesis. 2004, 104(9), 4125-49. 37. Yamada, J.; Akutsu, H.; Nishikawa, H.; Kikuchi, K. New Trends in the Synthesis of π-Electron Donors for Molecular Conductors and Superconductors. 2004, 104(11), 5057-83. 38. Iyoda, M.; Hasegawa, M.; Miyake, Y. Bi-TTF, BisTTF, and Related TTF Oligomers. 2004, 104(11), 5085113. 2886 J. Org. Chem., Vol. 70, No. 7, 2005
39. Jeppesen, J. O.; Nielsen, M. B.; Becher, J. Tetrathiafulvalene Cyclophanes and Cage Molecules. 2004, 104(11), 5115-31. 40. Fabre, J. M. Synthesis Strategies and Chemistry of Nonsymmetrically Substituted Tetrachalcogenafulvalenes. 2004, 104(11), 5133-50. 41. Gorgues, A.; Hudhomme, P.; Salle, M. Highly Functionalized Tetrathiafulvalenes: Riding Along the Synthetic Trail from Electrophilic Alkynes. 2004, 104(11), 5151-84. 42. Lorcy, D.; Bellec, N. Dithiadiazafulvalenes: Promising Precursors of Molecular Materials. 2004, 104(11), 5185-202. 43. Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B. Synthetic Preparation of N-Methyl-R-amino Acids. 2004, 104(12), 5823-46. 44. Chandrasekhar, V.; Boomishankar, R.; Nagendran, S. Recent Developments in the Synthesis and Structure of Organosilanols. 2004, 104(12), 5847-910. 45. Ma, J.-A.; Cahard, D. Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions. 2004, 104(12), 6119-46. Chemical Society Reviews 46. Hodgson, D. R. W.; Sanderson, J. M. The Synthesis of Peptides and Proteins Containing Non-Natural Amino Acids. 2004, 33(7), 422-30. 47. Echavarren, A. M.; Nevado, C. Non-Stabilized Transition Metal Carbenes as Intermediates in Intramolecular Reactions of Alkynes with Alkenes. 2004, 33(7), 431-6. 48. Concellon, J. M.; Rodriguez-Solla, H. β-Elimination Reactions by Using Samarium Diiodide. 2004, 33(9), 599-609. Chemistry - A European Journal 49. Panchaud, P.; Chabaud, L.; Landais, Y.; Ollivier, C.; Renaud, P.; Zigmantas, S. Radical Amination with Sulfonyl Azides: A Powerful Method for the Formation of C-N Bonds. 2004, 10(15), 3606-14. 50. Roesky, H. W.; Anantharaman, G.; Chandrasekhar, V.; Jancik, V.; Singh, S. Control of Molecular Topology and Metal Nuclearity in Multimetallic Assemblies: Designer Metallosiloxanes Derived from Silanetriols. 2004, 10(17), 4106-14. 51. Anorbe, L.; Dominguez, G.; Perez-Castells, J. Reorganization of Enynes Catalyzed by Platinum Salts. 2004, 10(20), 4938-43. 52. Szabo, K. J. Palladium-Catalyzed Electrophilic Allylation Reactions via Bis(allyl)palladium Complexes and Related Intermediates. 2004, 10(21), 5268-75. Chemistry of Heterocyclic Compounds 53. Borovlev, I. V.; Demidov, O. P. Diazapyrenes. 2003, 39(11), 1417-42. 54. Neilands, O. Phenyliodonium Derivatives of NHeterocycles and CH-Acids, Their Synthesis, and Their Use in the Chemistry of Heterocycles. (Review). 2003, 39(12), 1555-69.
55. Soldatenkov, A. T.; Temesgen, A. V.; Kolyadina, N. M. Oxidation of Heterocyclic Compounds by Permanganate Anion. (Review). 2004, 40(5), 537-60. 56. Sliwa, W. Heterocalixarenes. (Review). 2004, 40(6), 683-700. CHEMTRACTS: Organic Chemistry 57. Bandichhor, R.; Reiser, O. Cyclopropanation with Fischer Acyloxycarbene Complexes: Preparation of Cyclopropane and Cycloheptane-Fused γ-Lactones. 2004, 17(2), 67-71. 58. Hartung, R.; Paquette, L. Recent Synthetic Applications of the Tandem Staudinger/Aza-Wittig Reaction. 2004, 17(2), 72-82. 59. Prestat, G.; Poli, G. Transition Metal-Catalyzed Pseudo-Domino Sequences: The Development of a New Concept. 2004, 17(2), 97-103. Chirality 60. Formaggio, F.; Peggion, C.; Crisma, M.; Kaptein, B.; Broxterman, Q. B.; Mazaleyrat, J.-P.; Wakselman, M.; Toniolo, C. Recent Contributions of Electronic Circular Dichroism to the Investigation of Oligopeptide Conformations. 2004, 16(6), 388-97. Coordination Chemistry Reviews 61. Ungvary, F. Application of Transition Metals in Hydroformylation. Annual Survey Covering the Year 2003. 2004, 248(9-10), 867-80. 62. Omae, I. Intramolecular Five-Membered Ring Compounds and Their Applications. 2004, 248(11-12), 995-1023. 63. Soderberg, B. C. G. Transition Metals in Organic Synthesis. Highlights for the Year 2002. 2004, 248(1112), 1085-158. 64. King, R. B. The Beginnings of Terminal Vinylidene Metal Complex Chemistry Through the Dicyanomethylene/Oxygen Analogy: Dicyanovinylidene Transition Metal Complexes. 2004, 248(15-16), 1533-41. 65. Selegue, J. P. Metallacumulenes: From Vinylidenes to Metal Polycarbides. 2004, 248(15-16), 1543-63. 66. Kalck, P.; Urrutigoity, M. Asymmetric Catalysis Induced by the Substrate Itself. 2004, 248(21-24), 2193200. 67. Bedford, R. B.; Cazin, C. S. J.; Holder, D. The Development of Palladium Catalysts for C-C and C-Heteroatom Bond Forming Reactions of Aryl Chloride Substrates. 2004, 248(21-24), 2283-321. 68. Fogg, D. E.; dos Santos, E. N. Tandem Catalysis: A Taxonomy and Illustrative Review. 2004, 248(21-24), 2365-79. 69. Kamer, P. C. J.; van Rooy, A.; Schoemaker, G. C.; van Leeuwen, P. W. N. M. In Situ Mechanistic Studies in Rhodium Catalyzed Hydroformylation of Alkenes. 2004, 248(21-24), 2409-24. 70. Welton, T. Ionic Liquids in Catalysis. 2004, 248(2124), 2459-77. Current Organic Chemistry 71. Castellano, R. K. Progress Toward Understanding the Nature and Function of C-H‚‚‚O Interactions. 2004, 8(10), 845-65.
72. Katajisto, J.; Heinonen, P.; Loennberg, H. Pentaerythritol and Its Congeners: Versatile Building Blocks for the Construction of Oligomeric Bioconjugates and Small Molecule Libraries on a Solid Support. 2004, 8(11), 977-92. 73. Bellina, F.; Rossi, R. Mucochloric and Mucobromic Acids: Inexpensive, Highly Functionalized Starting Materials for the Selective Synthesis of Variously Substituted 2(5H)-Furanone Derivatives, Sulfur- or NitrogenContaining Heterocycles and Stereodefined Acyclic Unsaturated Dihalogenated Compounds. 2004, 8(12), 1089103. 74. Ayad, T.; Genisson, Y.; Baltas, M. Chemical Approaches Towards Synthesis of Some Naturally Occurring Iminosugars. 2004, 8(13), 1211-33. 75. Keglevich, G.; Forintos, H.; Koertvelyesi, T. Synthesis and Reactions of β-Oxophosphoranes/Ylides Containing a Cyclic or Acyclic P-Moiety. 2004, 8(13), 124561. 76. Camps, P.; Munoz-Torrero, D. Synthesis and Applications of (R)- and (S)-Pantolactone as Chiral Auxiliaries. 2004, 8(14), 1339-80. 77. Schneider, G.; Woelfling, J. Synthetic Cardenolides and Related Compounds. 2004, 8(14), 1381-403. 78. Abdel-Sattar, S.; Elgazwy, H. The Chemistry of Tricarballylic Acid (TCA). 2004, 8(14), 1405-23. 79. Rao, H. S. P.; Senthilkumar, S. P. Review on the Synthesis of 8-Azasteroids. 2004, 8(15), 1521-8. 80. Lesyk, R. B.; Zimenkovsky, B. S. 4-Thiazolidones: Centenarian History, Current Status and Perspectives for Modern Organic and Medicinal Chemistry. 2004, 8(16), 1547-77. 81. Aguilar-Martinez, M.; Macias-Ruvalcaba, N. A.; Bautista-Martinez, J. A.; Gomez, M.; Gonzalez, F. J.; Gonzalez, I. Review: Hydrogen Bond and Protonation as Modifying Factors of the Quinone Reactivity. 2004, 8(17), 1721-38. 82. Sicinska, D.; Rostkowski, M.; Paneth, P. Chlorine Isotope Effects on Chemical Reactions. 2005, 9(1), 7588. 83. Kouznetsov, V. V.; Mendez, L. Y. V.; Gomez, C. M. M. Recent Progress in the Synthesis of Quinolines. 2005, 9(2), 141-61. 84. Dalpozzo, R.; Bartoli, G. Bartoli Indole Synthesis. 2005, 9(2), 163-78. Current Organic Synthesis 85. Smith, K.; El-Hiti, G. A. Regioselective Control of Electrophilic Aromatic Substitution Reactions. 2004, 1(3), 253-74. 86. Melo, T. M. V. D. P. E.; Gonsalves, A. M. d. A. R. Exploiting 2-Halo-2H-azirine Chemistry. 2004, 1(3), 27592. 87. Knoelker, H.-J. Transition Metal Complexes in Organic Synthesis, Part 70. Synthesis of Biologically Active Carbazole Alkaloids Using Organometallic Chemistry. 2004, 1(4), 309-31. 88. Andrade, C. K. Z. Niobium Pentachloride in Organic Synthesis: Applications and Perspectives. 2004, 1(4), 333-53. 89. Maffei, M. Transition Metal-Promoted Syntheses of Vinylphosphonates. 2004, 1(4), 355-75. J. Org. Chem, Vol. 70, No. 7, 2005 2887
90. Keglevich, G.; Szelke, H.; Kovacs, J. Fragmentation-Related Phosphinylation and Phosphonylation of Nucleophiles Utilising the Bridging P-Unit of 2-Phosphabicyclo[2.2.2]Oct-5-Ene Derivatives. 2004, 1(4), 377-89. 91. Luo, S.; Peng, Y.; Zhang, B.; Wang, P. G.; Cheng, J.-P. Some New Trends and Recent Progress Towards Environmentally Benign Synthesis. 2004, 1(4), 405-29. Heterocycles 92. Katritzky, A. R.; Jiang, R.; Singh, S. K. Synthesis and Reactions of N-Ethynyl Heterocycles. 2004, 63(6), 1455-75. 93. Majumdar, K. C.; Mukhopadhyay, P. P.; Basu, P. K. Formation of Five- and Six-membered Heterocyclic Rings by Radical Cyclization. 2004, 63(8), 1903-58. 94. Sliwa, W.; Bachowska, B. Rotaxanes Containing Quaternary Azaaromatic Moieties. 2004, 63(9), 213158. 95. Froehner, W.; Krahl, M. P.; Reddy, K. R.; Knoelker, H.-J. Transition Metal Complexes in Organic Synthesis Part 73. Synthetic Routes to Naturally Occurring Furocarbazoles. 2004, 63(10), 2393-407. Journal of Fluorine Chemistry 96. Fustero, S.; Sanz-Cervera, J. F.; Piera, J.; SanchezRosello, M.; Chiva, G.; Simon-Fuentes, A. New Approaches to the Synthesis of Organofluorine Nitrogenated Derivatives. 2004, 125(4), 621-7. 97. Hoge, B.; Thosen, C.; Herrmann, T.; Panne, P.; Pantenburg, I. Strategies for the Synthesis of Chiral, Bidentate Bis(Perfluoroorganyl)Phosphane Ligands. 2004, 125(6), 831-51. Journal of Heterocyclic Chemistry 98. Levai, A. Synthesis of Heterocyclic Compounds by the Reactions of Exocyclic R,R-Unsaturated Ketones. 2004, 41(3), 299-310. 99. Levai, A. Synthesis of Isoflavones. 2004, 41(4), 449-60. 100. Negri, G.; Kascheres, C.; Kascheres, A. J. Recent Development in Preparation, Reactivity, and Biological Activity of Enaminoketones and Enaminothiones and Their Utilization to Prepare Heterocyclic Compounds. 2004, 41(4), 461-91.
105. Polishchuk, A. L.; Bartlett, K. L.; Friedman, L. A.; Jones, M., Jr. A p-Benzyne to m-Benzyne Conversion Through a 1,2-Shift of a Phenyl Group. Completion of the Benzyne Cascade. 2004, 17(9), 798-806. 106. Dvorko, G. F.; Ponomareva, E. A.; Ponomarev, M. E. Role of Nucleophilic Solvation and the Mechanism of Covalent Bond Heterolysis. 2004, 17(10), 825-36. 107. Bernasconi, C. F. The Principle of Nonperfect Synchronization: How Does it Apply to Aromatic Systems? 2004, 17(11), 951-6. 108. Chiavarino, B.; Crestoni, M. E.; Fornarini, S. Chemistry of Protonated Species in Gaseous Environments. 2004, 17(11), 957-66. 109. Schalley, C. A. Elements for the Construction of Molecular Devices: Template Effects and Self-Assembly. 2004, 17(11), 967-72. Natural Product Reports 110. Hanson, J. R. Steroids: Reactions and Partial Synthesis. 2004, 21(3), 386-94. 111. Jansen, B. J. M.; de Groot, A. Occurrence, Biological Activity and Synthesis of Drimane Sesquiterpenoids. 2004, 21(4), 449-77. 112. Steinbeck, C. Recent Developments in Automated Structure Elucidation of Natural Products. 2004, 21(4), 512-8. Organic Preparations International
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Procedures
113. Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.; Dingerdissen, U.; Boerner, A. Homogeneous Rhodium(I)-Catalyzed Reductive Aminations. 2004, 36(2), 99-120. 114. Khurana, J. M.; Chauhan, S.; Agrawal, A. Molybdenum in Organic Synthesis. A Review. 2004, 36(3), 201-76. 115. Olivera, R.; SanMartin, R.; Churruca, F.; Dominguez, E. Dibenzo[b,f]oxepines: Synthesis and Applications. A Review. 2004, 36(4), 297, 299-330. 116. Meusel, M.; Guetschow, M. Recent Developments in Hydantoin Chemistry. A Review. 2004, 36(5), 391443. 117. Su, W.; Zhong, W.; Bian, G.; Shi, X.; Zhang, J. Recent Advances in the Chemistry of Trichloromethyl Chloroformate and Bis(trichloromethyl) Carbonate. 2004, 36(6), 499-547. Pure and Applied Chemistry
Journal of Organometallic Chemistry 101. Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. Stable Non-N-Heterocyclic Carbenes (NonNHC): Recent Progress. 2004, 689(24), 3857-65. 102. Brown, J. M. Mechanism in Homogeneous Catalysis; NMR as a Prime Mover. 2004, 689(24), 400615. Journal of Physical Organic Chemistry 103. Kahr, B.; Kaminsky, W.; Claborn, K. Why Biphenyl Configuration Still Matters. 2004, 17(9), 735-9. 104. Simaan, S.; Biali, S. E. Conformational Analysis of Calixarene Derivatives Substituted at the Methylene Bridges. 2004, 17(9), 752-9. 2888 J. Org. Chem., Vol. 70, No. 7, 2005
118. Wong, M. S.; Li, Z. H. Multifunctional Properties of Monodisperse End-Functionalized Oligophenylenevinylenes. 2004, 76(7-8), 1409-19. 119. Beletskaya, I. P.; Averin, A. D. PalladiumCatalyzed Arylation of Linear and Cyclic Polyamines. 2004, 76(9), 1605-19. 120. Charushin, V. N.; Chupakhin, O. N. SNH Methodology and New Approaches to Condensed Heterocyclic Systems. 2004, 76(9), 1621-31. 121. Makhova, N. N.; Ovchinnikov, I. V.; Kulikov, A. S.; Molotov, S. I.; Baryshnikova, E. L. Monocyclic and Cascade Rearrangements of Furoxans. 2004, 76(9), 1691703. 122. Nifantiev, N. E.; Sherman, A. A.; Yudina, O. N.; Cheshev, P. E.; Tsvetkov, Y. E.; Khatuntseva, E. A.;
Kornilov, A. V.; Shashkov, A. S. New Schemes for the Synthesis of Glycolipid Oligosaccharide Chains. 2004, 76(9), 1705-14. 123. Sigel, H. Acid-Base Properties of Purine Residues and the Effect of Metal Ions: Quantification of Rare Nucleobase Tautomers. 2004, 76(10), 1869-86. 124. Reichardt, C. Pyridinium N-Phenoxide Betaine Dyes and Their Application to the Determination of Solvent Polarities. Part XXVIII. 2004, 76(10), 190319. Russian Chemical Reviews 125. Dunina, V. V.; Gorunova, O. N. Phosphapalladacycles: Preparation Routes. 2004, 73(4), 309-50. 126. Bregadze, V. I.; Timofeev, S. V.; Sivaev, I. B.; Lobanova, I. A. Substitution Reactions at Boron Atoms in Metallacarboranes. 2004, 73(5), 433-53. 127. Banerjee, A. K.; Poon, P. S.; Laya, M. S.; Vera, W. J. Synthesis of Allylic Alcohols from Alkenes and Their Derivatives. 2004, 73(7), 621-36. 128. Litvinov, V. P. Chemistry and Biological Activities of 1,8-Naphthyridines. 2004, 73(7), 637-69. 129. Pokholenko, A. A.; Voitenko, Z. V.; Kovtunenko, V. A. Pyrido- and Pyrimidoisoindoles: Methods of Synthesis and Properties. 2004, 73(8), 771-84. Science 130. Jutzi, P.; Mix, A.; Rummel, B.; Schoeller, W. W.; Neumann, B.; Stammler, H.-G. The (Me5C5)Si+ Cation: A Stable Derivative of HSi+. 2004, 305(5685), 84951. 131. Resa, I.; Carmona, E.; Gutierrez-Puebla, E.; Monge, A. Decamethyldizincocene, a Stable Compound of Zn(I) with a Zn-Zn Bond. 2004, 305(5687), 1136-8. 132. Gartner, Z. J.; Tse, B. N.; Grubina, R.; Doyon, J. B.; Snyder, T. M.; Liu, D. R. DNA-Templated Organic Synthesis and Selection of a Library of Macrocycles. 2004, 305(5690), 1601-5. 133. West, R. Chemistry: Japan Bats a Triple. 2004, 305(5691), 1724-5. 134. Sorensen, E. J.; Sammis, G. M. Chemistry: A Dash of Proline Makes Things Sweet. 2004, 305(5691), 1725-6. 135. Northrup, A. B.; MacMillan, D. W. C. Two-Step Synthesis of Carbohydrates by Selective Aldol Reactions. 2004, 305(5691), 1752-5. Synlett 136. Belvisi, L.; Colombo, L.; Manzoni, L.; Potenza, D. Design, Synthesis, Conformational Analysis and Application of Azabicycloalkane Amino Acids as Constrained Dipeptide Mimics. 2004, (9), 1449-71. 137. Wei, C.; Li, Z.; Li, C.-J. The Development of A3Coupling (Aldehyde-Alkyne-Amine) and AA3-Coupling (Asymmetric Aldehyde-Alkyne-Amine). 2004, (9), 147283. 138. Adak, A. K. Phenyl Dichlorophosphate - A Versatile Reagent. 2004, (9), 1651-2. 139. Doye, S. Development of the Ti-Catalyzed Intermolecular Hydroamination of Alkynes. 2004, (10), 165372.
140. Lee, H.-S.; Kang, S. H. Synthesis of Physiologically Potent β-Amino Alcohols. 2004, (10), 1673-85. 141. Iorga, B.; Campagne, J.-M. Ethyl Propiolate: A Simple and Convenient Peptide Coupling Reagent. 2004, (10), 1826-8. 142. Wan, Q. Di-n-butyltin Oxide (DBTO). 2004, (10), 1847-8. 143. Soldaini, G. Methyltrioxorhenium (MTO). 2004, (10), 1849-50. 144. Sasaki, M.; Fuwa, H. Total Synthesis of Polycyclic Ether Natural Products Based on Suzuki-Miyaura CrossCoupling. 2004, (11), 1851-74. 145. Yamago, S. Novel Group-Transfer Radical Reactions with Organotelluriums. 2004, (11), 1875-90. 146. Prabhakaran, R. Shvo’s Diruthenium Complex [(η5-C4Ph4COHOCC4Ph4-η5)(µ- H)(CO)4Ru2]. 2004, (11), 2048-49. 147. Ferreira, F.; Denichoux, A.; Chemla, F.; Bejjani, J. Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems. 2004, (12), 205165. 148. Totani, K.; Takao, K.-i.; Tadano, K.-i. Sugar as a Tool for Asymmetric Synthesis: Some Effective Approaches. 2004, (12), 2066-80. SynthesissStuttgart 149. Clayden, J.; Kenworthy, M. N. Cyclisations of Organolithiums onto Aromatic Rings. 2004, (11), 172136. 150. Salom-Roig, X. J.; Denes, F.; Renaud, P. Radical Cyclization of Halo Acetals: The Ueno-Stork Reaction. 2004, (12), 1903-28. 151. Hoffmann, R. W. Stereoselective Synthesis Using Diastereotopic Groups. 2004, (13), 2075-90. 152. El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Synthesis of Azaspiro[4.4]nonanes as Key Structures of Several Bioactive Natural Products. 2004, (14), 224962. 153. Bellina, F.; Carpita, A.; Rossi, R. Palladium Catalysts for the Suzuki Cross-Coupling Reaction: An Overview of Recent Advances. 2004, (15), 2419-40. 154. Rodriguez, S.; Wipf, P. Oxidative Spiroacetalizations and Spirolactonizations of Arenes. 2004, (17), 2767-83. 155. Riant, O.; Mostefai, N.; Courmarcel, J. Recent Advances in the Asymmetric Hydrosilylation of Ketones, Imines, and Electrophilic Double Bonds. 2004, (18), 2943-58. Tetrahedron 156. Zhou, P.; Chen, B.-C.; Davis, F. A. Recent Advances in Asymmetric Reactions Using Sulfinimines (NSulfinyl Imines). 2004, 60(37), 8003-30. 157. Silveira, C. C.; Braga, A. L.; Kaufman, T. S.; Lenardao, E. J. Synthetic Approaches to 2-Tetralones. 2004, 60(38), 8295-328. 158. Erdik, E. Electrophilic R-Amination of Carbonyl Compounds. 2004, 60(40), 8747-82. 159. Zificsak, C. A.; Hlasta, D. J. Current Methods for the Synthesis of 2-Substituted Azoles. 2004, 60(41), 8991-9016. J. Org. Chem, Vol. 70, No. 7, 2005 2889
160. Ocampo, R.; Dolbier, W. R., Jr. The Reformatsky Reaction in Organic Synthesis. Recent Advances. 2004, 60(42), 9325-74. 161. Bonaga, L. V. R.; Krafft, M. E. When the PausonKhand and Pauson-Khand Type Reactions Go Awry: A Plethora of Unexpected Results. 2004, 60(44), 9795-833. 162. Bracca, A. B. J.; Kaufman, T. S. Synthetic Approaches to Carnegine, a Simple Tetrahydroisoquinoline Alkaloid. 2004, 60(47), 10575-610. 163. Howell, A. R.; So, R. C.; Richardson, S. K. Approaches to the Preparation of Sphinganines. 2004, 60(50), 11327-47.
165. Ema, T. Rational Strategies for Highly Enantioselective Lipase-Catalyzed Kinetic Resolutions of Very Bulky Chiral Compounds: Substrate Design and HighTemperature Biocatalysis. 2004, 15(18), 2765-70. 166. Dzyuba, S. V.; Klibanov, A. M. Stereoselective Oxidations and Reductions Catalyzed by Nonredox Proteins. 2004, 15(18), 2771-77. 167. Phillips, R. S. Synthetic Applications of Tryptophan Synthase. 2004, 15(18), 2787-92. 168. Ghanem, A.; Aboul-Enein, H. Y. Lipase-Mediated Chiral Resolution of Racemates in Organic Solvents. 2004, 15(21), 3331-51.
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Monographs 170. Atta ur, R.; Ed. Bioactive Natural Products (Part J). [In: Stud. Nat. Prod. Chem. 2003; 29]. Elsevier Science: Amsterdam, Netherlands, 2003. 171. Barrett, G. C.; Davies, J. S. Amino Acids, Peptides and Proteins. Vol. 34. Royal Society of Chemistry: Cambridge, U.K., 2003. 172. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids, Handbook. Birkhaeuser Verlag: Basel, Switzerland, 2004. 173. Budzikiewicz, H. Siderophores of the Pseudomonadaceae Sensu Stricto (Fluorescent and Non-Fluorescent Pseudomonas spp). [In: Progress in the Chemistry of Organic Natural Products. 2004, 87]. Herz, W., Falk, H., Kirby, G. W., Eds., Springer-Verlag: Vienna, Austria, 2004. 174. Cironi, P.; Albericio, F.; Alvarez, M. Lamellarins: Isolation, Activity and Synthesis. [In Progress in Heterocyclic Chemistry. 2004, 16] Gribble, G. W., Joule, J., Eds., Elsevier: Oxford, U. K., 2004. 175. Flapan, E. When Topology Meets Chemistry: A Topological Look at Molecular Chirality. Cambridge University Press: Cambridge, U.K., 2000. 176. Flessner, T.; Jautelat, R.; Scholz, U.; Winterfeldt, E. Cephalostatin Analogues - Synthesis and Biological Activity. [In: Progress in the Chemistry of Organic Natural Products. 2004, 87]. Herz, W., Falk, H.,
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Kirby, G. W., Eds., Springer-Verlag: Vienna, Austria, 2004. 177. Gossauer, A. Monopyrrolic Natural Compounds Including Tetramic Acid Derivatives. [In: Progress in the Chemistry of Organic Natural Products. 2003, 86]. Herz, W., Falk, H., Kirby, G. W., Eds., Springer-Verlag: Vienna, Austria, 2003. 178. Green, M. Organometallic Chemistry. A Review of the Literature Published During 2001. Vol. 31. Royal Society of Chemistry: Cambridge, U.K., 2004. 179. Harrowven, D. C.; Sutton, B. J. Radical Additions to Pyridines, Quinolines and Isoquinolines. [In Progress in Heterocyclic Chemistry. 2004, 16] Gribble, G. W., Joule, J., Eds. 2004. 180. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Eds. Comprehensive Asymmetric Catalysis, Supplement: Volume 1. Springer-Verlag: Berlin, Germany, 2004. 181. Jutzi, P.; Schubert, U.; Eds. Silicon Chemistry: From the Atom to Extended Systems. Wiley-VCH: Weinheim, Germany, 2003. 182. Osborn, H. M.; Khan, T. H. Oligosaccharides: Their Synthesis and Biological Role. Oxford University Press: New York, 2000. 183. Steglich, W.; Fugmann, B.; Lang-Fugmann, S. ROMPP Encyclopedia Natural Products. Thieme Verlag: Stuttgart, Germany, 2000.
Index Acetals, halo, radical cyclization, 150 Acylhydrazones, allylation, 7 Acyloxycarbene complexes, Fischer-, 57 Alcohols, oxidation, with hypervalent iodine, 6 Aldehyde-alkyne-amine coupling, 137 Alkaloids, furocarbazoles, 95 marine, book, 174 polyhydroxylated, 74 synthesis, with sulfonyl azides, 49 tetrahydroisoquinoline, 162 Alkenes, hydroformylation, with Rh, 69 oxidation, 143 Alkyl halides, unactivated, cross coupling, Ni-catalyzed, 12 Alkylboranes, Suzuki-Miyaura crosscoupling, 144 Alkylidenecarbenes, 34 Alkylidenecarbenoids, 34 Alkynes, hydroamination, 139 reaction with alkenes, 47 Allose, short synthesis with proline, 134 Allylation, pincer complex catalysts, 52 with Pd, 52 Allylic alcohols, from alkenes, 127 from epoxides, 127 Amination, reductive, with Rh, 113 with sulfonyl azides, 49 Amines, allylic, fluorinated, 96 cross coupling, with Pd, 15 Amino acids, book, 171 N-methylation, 43 N-protected, coupling, 141 Amino alcohols, β-, synthesis, 140 Amino nitriles, R-, from tertiary amines, 17 Androgens, 110 Arenes, spiroacetalizations, 154 spirolactonizations, 154 Aromatic substitution, ortho-lithiation, 85 regioselective, 85 Aromatics, acetoxylation, 9 ammoxidation, 9 bicyclic, synthesis, 149 hydroxylation, 9 Moebius, 18 organolithium, cyclization, 149 oxidation, 9 self-assembled helix, 31 transition state, 107 Aryl chlorides, C-C bond formation, 67 C-heteroatoms bonds, 67 Asymmetric catalysis, book, 180 Asymmetric self-catalysis, 66 Asymmetric synthesis, dual Lewis acid/ base, 19 Azabicycloalkane amino acids, 136 Azaspirononanes, 152 Azasteroids, 8-, 79 Azidating agents, sulfonyl azides, 49 Azinoisoindoles, 129 Aziridines, acetylinic, 147 Azirines, 2H-, 86 Azoles, 2-, synthesis, 159 monocyclic rearrangement, 121 Baeyer-Villiger Reaction, green, 35 Bartoli reaction, 84 Benzene acetyloxylation, 9
Benzenium ion, 108 Benzynes, phenyl group shift, 105 Betaine dye, for solvent polarity, 124 Betaines, 54 Biocatalysts, nonredox proteins, 166 Biphenyl dyes, 103 Bis(allyl)palladium complexes, 52 Bis(trichloromethyl) carbonate, 117 Buchwald-Hartwig amination, 15 Bufadienolides, 77 CdC bonds, via β-elimination, SmI2, 48 Calixarene derivatives, conformation, 104 heterocyclic, 56 Carbazole alkaloids, synthesis, 87 Carbenes, alkylphosphino-, 101 aminophosphino, 101 aryl-, 101 arylamino-, 101 metal cyclopropyl-, 47 Carbohydrates, via two step aldol coupling, 135 Carbonyls, electrophylic R-amination, 158 Carboxylic acids, fluorinated, 96 Cardenolides, 77 Carnegine, 162 Carotenoids, book, 172 Catalysis, tandem, 68 Cephalostatin analogs, book, 176 Chiral compounds, bulky, kinetic resolution, 165 Chiral resolution, lipase-catalyzed, 168 membranes, 27 Chlorine isotope effects, 82 Chlorohydrins, acetylinic, 147 Cholestanes, 110 Cholic acid steroids, 110 Ciguatoxin CTX3C, synthesis, 4 synthesis, 144 Cross-coupling reactions, 10-11 high turnover, with Pd, 14 Cycloalkanes, vinyl-, synthesis, 51 Cyclophanes, tetrathiafulvalene, 39 Cyclopropanation, 57 Decamethyldizincocene, 131 Decamethylsilicocene cation, 130 Diamines, 1,2-, unsymmetrical, synthesis, 17 Dianions, cyclization, 36 Diazapyrenes, 53 Dibenzo[b,f]oxepines, 115 Dicyanovinylidene complexes, 64 Dimethylformamide organosilicon reagents, 7 Di-n-butyltin oxide, DBTO, 142 Diols, monophosphorylation, 138 Dipeptide mimics, 136 Diterpenoids, Elisabethin A, synthesis, 22 Dithiadiazafulvalenes, 42 DNA template synthesis, 23, 132 Enaminoesters, cyclic, β-, 100 Enaminoketones, 100 Enaminothiones, 100 Enediynes, cyclization, computational studies, 5 Enyne cycloisomerization, 51 Enyne-allenes, cyclization, computational studies, 5 Estrogens, 110
Ethyl propiolate, peptide coupling, 141 Fluorination, asymmetric, 45 Fluoroalkylation, 45 Fullerenes, C50, 20 synthesis, 24 Furannone derivatives, 73 Furocarbazoles, synthesis, 95 Furoxans, cascade rearrangement, 121 monocyclic rearrangement, 121 Glucose, short synthesis with proline, 134 Green synthesis, 91 Haloazirines, 86 Heck reaction, 11 asymmetric, 13 high turnover, with Pd, 14 Henry reaction, chiral catalysts, 30 Heterocalixarenes, 56 Heterocycles, ethynyl, 92 from enaminoketones, 100 from enaminothiones, 100 from exocyclic unsaturated ketones, 98 fused, SNH synthesis, 120 N-, phenyliodonium, 54 oxidation, with permanganate anion, 55 via radical cyclization, 93 Heterocyclic carbenes, N-, catalysts, 25 N-, reagents, 25 Heterolysis, solvent effects, 106 Hexoses, synthesis, 134 Homogeneous catalysis, NMR, 102 Homopropargylic systems, steroselective synthesis, 147 Hydantoin chemistry, 116 Hydantoin hydrolyzing enzyme, 164 Hydroformylation, with transition metals, 61 Hydrogen bonds, C-H‚‚‚O, 71 Imines, hydrosilylation, asymmetric, 155 Iminophosphoranes, β-, ylides, 75 Iminosugars, synthesis, 74 Indoles, Bartoli synthesis, 84 Intermolecular interactions, quantification, 29 Iodosylbenzene, with CH-acids, 54 Iodoxybenzoic acid, alcohol oxidation, 6 Ionic liquids, catalysis, 70, 169 Ionic solvents, decomposition, 28 Isoflavones, 99 Isoindolones, from benzamides, 149 Isoquinolines, radical additions, book, 179 Ketones, halogenation, 138 hydrosilylation, asymmetric, 155 unsaturated, exocylic, 98 Lactones, from radical cyclization of halo acetals, 150 Lamellarins, book, 174 Lanthanide triflate catalysis, 91 Macrocyles, DNA-, from nucleic acid libraries, 132 Mannose, short synthesis with proline, 134 Membranes, chiral resolution, 27 Metallacarboranes, substitution, 126 Metallacumulenes, 65 Metallocyclopentenes, 47
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Metallosiloxanes, from silanetriols, 50 Methyltrioxorhenium, alkene epoxidation, 143 Microwaves, in organic synthesis, 33 Moebius aromatics, 18 Molecular chirality, book, 175 Molecular conductors, π electron donors, 37 Molecular crystals, intersolid reactions, 16 Molecular devices, 109 Molybdenum, in synthesis, 114 Mucobromic acid, 73 Mucochloric acid, 73 Naphthyridines, 128 Natural products, automated structure elucidation, 112 bioactive, book, 170 book, 183 Niobium pentachloride, 88 Nitroalcohols, chiral, from nitroalkanes, 30 Nitroaldol reaction, chiral catalysts, 30 Nitroxyl radicals, oxidation, 8 Nucleic acids, acid-base properties, 123 Oligomeric bioconjugates, 72 Oligopeptide conformation, ECD, 60 Oligophenylenevinylenes, 118 Oligosaccharides, book, 182 glycolipid, 122 Open framework materials, 1 Organoboron, organic cross-coupling, 153 Organocatalysis, 26 green, 91 neutral coordinate, 7 Organofluorine nitrogenated compound, 96 Organometallics, book, 178 five-membered rings, 62 Organophosphates, 1 Organophosphorus chemistry, 3 Organosilanols, 44 secondary building units, 1 Organosilicon compounds, Si-Si triple bond, 133 Organostannanes, stille reaction, 21 Organotellurium compounds, 145 Oxiranes, acetylinic, 147 Oxophosphoranes, β-, ylides, 75 Palladacycles, catalysts, 14 with aryl chlorides, 67
Pantolactone, chiral auxiliary, 76 Pauson-Khand reaction, 161 Pentaerythritol, chiral synthons, 72 Peptides, book, 171 chirality, 60 non-natural amino acids, 46 Peptidomimetics, 136 Perfluoroalkylation, carbene, 45 radical, 45 Phenyl dichlorophosphate, 138 Phosphabicyclooctenes, photolysis, 90 Phosphane ligands, chiral, bidentate, 97 Phosphapalladacycles, preparation, 125 Phosphate clusters, 1 Phosphate secondary building units, 1 Phosphines, cyclopalladation, 125 Phosphinylation, nucleophiles, 90 Phospholes, transient 2H-, 3 Phosphonylation, nucleophiles, 90 Platinum-cinchona chiral catalyst, 2 Polyamines, arylation, with Pd, 119 Polycarbide metal complexes, 65 Polycyclic ethers, 144 Polycycloalkanes, synthesis, 51 Pregnanes, 110 Proline, in aldol additions, 134 Propargylic acid, stereoselective synthesis, 147 Proteins, book, 171 non-natural amino acids, 46 nonredox, chiral templates, 166 nonredox, oxidation catalysts, 166 Pseudo-domino sequences, with transition metals, 59 Pseudomonads, book, 173 Purines, acid-base properties, 123 Pyrazines, bissteroidal, book, 176 Pyridines, radical additions, book, 179 Pyridoisoindoles, 129 Pyrimidoisoindoles, 129 Pyrroles, book, 177 Pyrrolidinedicarboxylic acids, synthesis, 149 Quinolines, radical additions, book, 179 synthesis, 83 Quinones, reduction, 81 R-hydroxy, 81 Quinoxalines, synthesis, 138 Reformatsky reaction, 160 Rotaxanes, quaternary azaaromatic, 94 Sesquiterpenoids, drimane, 111
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Shvo’s diruthenium complex, 146 Silicon chemistry, book, 181 Solventless reactions, 16 Solvents, ionic liquids, 70, 169 Sphinganines, preparation, 163 Spiroacetalizations, of arenes, 154 Spirolactonization, of arenes, 154 Staudinger/Aza-Wittig tandem reaction, 58 Stereoselective synthesis, using diastereotopic groups, 151 Steroids, 110 Stille reaction, copper effect, 21 mechanism, 21 Sugar templates, chiral, 148 Sulfinimines, natural product synthesis, 156 Suzuki cross-coupling, Pd catalyst, 153 Tandem reactions, Staudinger/Aza-Wittig, 58 Tetrachalcogenafulvalenes, nonsymmetrical, 40 Tetrahydroxycalixarene derivatives, conformation, 104 Tetralones, 2-, synthesis, 157 Tetrathiafulvalenes, 38 cage molecules, 39 cyclophanes, 39 functionalized, 41 Tetrodotoxin, synthesis, 32 Thiazolidones, 80 Thiouracils, fluorinated, 96 Transition metals, in synthesis, 63 Tricarballylic acid, substituted, 78 Trichloroacetimidates, intramolecular amination, 140 Trichloromethyl chloroformate, 117 Trifluoromethylation, 45 Tryptophan analogs, synthesis, 167 Tryptophan synthase, enzyme catalysis, 167 Ueno-Stork reaction, 150 Uracils, fluorinated, 96 Vinylphosphonates, synthesis with transition metals, 89 Vitamin D analogs, 110 Ylides, phosphorus, β-imino, 75 phosphorus, β-oxo, 75 JO0560207
