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Direct Catalytic Asymmetric Aldol-Tishchenko Reaction

Vijay Gnanadesikan, Yoshihiro Horiuchi, Takashi Ohshima and Masakatsu Shibasaki*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan, Email: mshibasamol.f.u-tokyo.ac.jp

V. Gnanadesikan, Y. Horiuchi, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 7782-7783.

DOI: 10.1021/ja047906f (free Supporting Information)


Abstract

A direct catalytic asymmetric aldol reaction of propionate equivalent was achieved via the aldol-Tishchenko reaction. Coupling an irreversible Tishchenko reaction to a reversible aldol reaction overcame the retro-aldol reaction problem and thereby afforded the products in high enantio and diastereoselectivity.

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proposed mechanism



Key Words

Tishchenko Reaction, 1,3-Diols


ID: J48-Y2004-1520