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Highly Diastereo- and Enantioselective Direct Aldol Reactions in Water

Yujiro Hayashi*, Tatsunobu Sumiya, Junichi Takahashi, Hiroaki Gotoh, Tatsuya Urushima, Mitsuru Shoji

*Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, E-mail: hayashici.kagu.tus.ac.jp

Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. Int. Ed., 2006, 45, 958-961.

DOI: 10.1002/anie.200502488 (free Supporting Information)


Abstract

Siloxyproline organocatalysts promote the aldol reaction in the presence of water without organic solvent offering high enantioselectivity and diastereoselectivity. The catalysts can easily be prepared in large quantities from the commercially available trans-4-hydroxyproline.

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Key Words

aldol reaction, asymmetric synthesis, diastereoselectivity, organocatalysis, solvent effects


ID: J06-Y2006-320