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Review | Regular issue | Vol 75, No. 4, 2008, pp.757-797
Published online, 26th November, 2007
DOI: 10.3987/REV-07-621
Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2.

Hiyoshizo Kotsuki,* Hideaki Ikishima, and Atsushi Okuyama

*Laboratory of Natural Product Chemistry, Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan


Organocatalytic asymmetric synthesis has been extensively studied and several important procedures for preparing optically active organic compounds have been developed. Research activities in this area have progressed rapidly in the last ten years. This review addresses the most significant advances in asymmetric synthesis using proline and related chiral organocatalysts, mainly from the viewpoint of synthetic applications. This includes (1) Mannich reactions, (2) Michael addition reactions, (3) α-oxidation, (4) α-amination, (5) α-sulfenylation / selenenylation, (6) α-halogenation, (7) cycloaddition reactions, and (8) miscellaneous reactions such as C-C bond formation, epoxidation / oxidation, and reduction.