Catalysis in Asymmetric Synthesis by Caprio V., Williams J.

By Caprio V., Williams J.

Content material: Preface to the second one variation. Preface to the 1st version. 1 advent. 1.1 Reactions Amenable to uneven Catalysis. 1.2 project of (R) and (S) Stereochemical Descriptors. Futher examining. References. 2 aid of Alkenes. 2.1 uneven Hydrogenation with Rhodium Complexes. 2.2 uneven Hydrogenation with Ruthenium Catalysts. 2.3 Alkene Hydrogenation with Titanium and Zirconium Catalysts. 2.4 Alkene Hydrogenation with Iridium Catalysts. 2.5 Alkene Hydrogenation with Organocatalysts. 2.6 Alkene Hydrosilylation. 2.7 Alkene Hydroboration. 2.8 Hydroamination. 2.9 Hydroformylation. 2.10 Hydroacylation of Alkenes. 2.11 Hydrocyanation of Alkenes. References. three relief of Ketones and Imines. 3.1 Hydrogenation of Ketones. 3.2 Hydrogenation and move Hydrogenation of Imines and comparable Compounds. 3.3 move Hydrogenation of Ketones. 3.4 Heterogeneous Hydrogenation. 3.5 aid of Ketones utilizing Enantioselective Borohydride Reagents. 3.6 Hydrosilylation of Ketones. 3.7 Hydrosilylation of Imines and Nitrones. References. four Epoxidation. 4.1 Epoxidation of Allylic Alcohols. 4.2 Epoxidation with Metal(salen) Complexes. 4.3 Epoxidation utilizing Metal-Porphyrin-Based Catalysts. 4.4 OtherMetal-Catalysed Epoxidations of Unfunctionalised Olefins. 4.5 Epoxidation of Electron-Deficient Alkenes. 4.6 Epoxidation with Iminium Salts. 4.7 Epoxidation with Ketone Catalysts. 4.8 Epoxidation of Aldehydes. 4.9 Aziridination of Alkenes. 4.10 Aziridination of Imines. References. five additional Oxidation Reactions. 5.1 Dihydroxylation. 5.2 Aminohydroxylation. 5.3 alpha-Heterofunctionalisation of Aldehydes and Ketones. 5.4 Oxidation of C-H. 5.5 Baeyer-Villiger Oxidation. 5.6 Oxidation of Sulfides. References. 6 Nucleophilic Addition to Carbonyl Compounds. 6.1 Addition of Organozincs to Carbonyl Compounds. 6.2 Addition of Cyanide to Aldehydes and Ketones. 6.3 Allylation of Aldehydes. 6.4 Hydrophosphonylation of Aldehydes. 6.5 Nucleophilic Additions to Imines. References. 7 The Aldol and comparable Reactions. 7.1 The Aldol response. 7.2 Isocyanide and comparable Aldol Reactions. 7.3 The Nitroaldol response. 7.4 Addition of Enolates to Imines. 7.5 Darzens Condensation. 7.6 Morita-Baylis-Hillman response. 7.7 Carbonyl-Ene Reactions. References. eight Cycloadditions. 8.1 Diels-Alder Reactions. 8.2 Inverse Electron call for Diels-Alder Reactions. 8.3 Hetero-Diels-Alder Reactions. 8.4 1,3-Dipolar Cycloaddition Reactions. 8.5 [2+2] Cycloadditions. 8.6 Pauson-Khand-Type Reactions. References. nine Catalytic Reactions concerning Carbenes and Ylides. 9.1 Cyclopropanation. 9.2 Insertion Reactions. 9.3 uneven Ylide Reactions. References. 10 Catalytic Carbon-Carbon Bond-Forming Reactions. 10.1 Cross-Coupling Reactions. 10.2 Metal-Catalysed Allylic Substitution. 10.3 Heck Reactions. 10.4 Alkylmetalation of Alkenes. References. eleven Conjugate Addition Reactions. 11.1 Conjugate Addition of Enolates. 11.2 Conjugate Addition of Sulfur Nucleophiles. 11.3 Conjugate Addition of Nonstabilised Nucleophiles. 11.4 Conjugate Addition with Nitrogen-Based Nucleophiles and Electrophiles. References. 12 extra Catalytic Reactions. 12.1 Isomerisations and Rearrangements. 12.2 Deprotonation Reactions. 12.3 Protonation Reactions. 12.4 Alkylation and Allylation of Enolates. 12.5 Formation of Alkenes. 12.6 Oxyselenylation-Elimination Reactions. 12.7 The Benzoin Condensation. 12.8 Ester Formation and Hydrolysis. 12.9 Ring-Opening of Epoxides. References. Index

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E. Cesaroth, R. B. Kagan, Angew. Chem,. Int. Ed. , 1979, 18, 779. 44 Catalysis in Asymmetric Synthesis 66. R. L. C. E. Welker, D. Bl¨aser and R. Boese, J. Am. Chem. , 1987, 109, 8105 67. F. R. W. P. Wild, L. Zsolnai, G. Huttner and H. H. Brintzinger, J. Organomet. , 1982, 232, 233. 68. R. D. Broene and S. L. Buchwald, J. Am. Chem. , 1993, 115, 12569. 69. R. Waymouth and P. Pino, J. Am. Chem. , 1990, 112, 4911. 70. V. P. Conticello, L. Brard, M. A. Giardello, Y. Tsuji, M. Sabat, C. L. Stern and T.

S. Tedrow and K. R. Campos, J. Am. Chem. , 2003, 125, 3534. 16. For reviews on combinatorial asymmetric catalysis see: (a) M. T. Reetz, Angew. Chem. Int. , 2001, 40, 284. (b) M. T. Reetz, Angew. , 2002, 41, 1335. (c) C. Gennari and U. Piarulli, Chem. , 2003, 103, 3071. 17. (a) M. T. Reetz and X. Li, Tetrahedron, 2004, 60, 9709. (b) R. Hoen, T. TiemersmaWegman, B. Procuranti, L. Lefort, J. G. de Vries, A. J. Minnaard and B. L. Feringa, Org. Biomol. , 2007, 5, 267. 18. M. J. Burk, S. Feng, M. F. Gross and W.

E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, 1999, 351. (b) C. M. Crudden and D. Edwards, Eur. J. Org. , 2003, 4695. 103. T. Hayashi, Y. Matsumoto and Y. Ito, J. Am. Chem. , 1989, 111, 3426. 104. J. M. Brown, D. I. Hulmes and T. P. Layzell, J. Chem. , Chem. , 1993, 1673. 105. J. M. Valk, G. A. Whitlock, T. P. Layzell and J. M. Brown, Tetrahedron: Asymmetry, 1995, 6, 2593. 106. A. Schnyder, L. Hintermann and A. Togni, Angew. Chem. Int. Ed. , 1995, 34, 931. 107. A. Schnyder, A.

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