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Catalytic Generation of Indium Hydride in a Highly Diastereoselective Reductive Aldol Reaction

Ikuya Shibata*, Hirofumi Kato, Tatsuya Ishida, Makoto Yasuda, Akio Baba

*Department of Molecular Chemistry, Science and Technology Center for Atom, Molecules and Ions Control, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: shibatachem.eng.osaka-u.ac.jp

I. Shibata, H. Kato, T. Ishida, M. Yasuda, A. Baba, Angew. Chem. Int. Ed., 2004, 43, 711-714.

DOI: 10.1002/anie.200352738 (free Supporting Information)


Abstract

An Et3SiH-promoted diastereoselective reductive aldol reaction has been developed using InBr3 as a catalyst. This three-component reaction afforded only silyl aldolates as products without any side reactions.

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proposed mechanism



Key Words

aldol reaction, diastereoselectivity, hydroxyketones, indium, triethylsilane, reductive aldol addition, Multicomponent Reactions


ID: J06-Y2004-090