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Combined Proline-Surfactant Organocatalyst for the Highly Diastereo- and Enantioselective Aqueous Direct Cross-Aldol Reaction of Aldehydes

Yujiro Hayashi*, Seiji Aratake, Tsubasa Okano, Junichi Takahashi, Tatsunobu Sumiya, Mitsuru Shoji

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

Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. Int. Ed., 2006, 45, 5527-5529.

DOI: 10.1002/anie.200601156 (free Supporting Information)


Abstract

A catalytic, direct asymmetric cross-aldol reaction of two different aldehydes in the presence of water is catalyzed by a novel combined proline-surfactant organocatalyst. Neither an organic cosolvent nor additional acid is necessary.

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Key Words

aldol addition, asymmetric synthesis, green chemistry, organocatalysis, surfactants, 1,3-diols, sodium borohydride


ID: J06-Y2006-2490