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Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes

Yoshihiro Inamoto, Yoshihiro Nishimoto, Makoto Yasuda and Akio Baba*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

Y. Inamoto, Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett., 2012, 14, 1168-1171.

DOI: 10.1021/ol3001443 (free Supporting Information)


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Abstract

An indium triiodide catalyst promoted the Mukaiyama Aldol Reaction of silyl enolates with esters to form β-hydroxycarbonyl compounds in the presence of hydrosilanes. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups, such as alkenyl, alkynyl, chloro, and hydroxy.

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Key Words

Mukaiyama Aldol Addition, Silanes, β-Hydroxycarbonyl Compounds


ID: J54-Y2012-0510