Catalytic Asymmetric Synthesis of 2,2-Disubstituted Terminal Epoxides via Dimethyloxosulfonium Methylide Addition to Ketones

Toshihiko Sone, Akitake Yamaguchi, Shigeki Matsunaga* and Masakatsu Shibasaki*

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

T. Sone, A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2008, 130, 10078-10079.

DOI: 10.1021/ja803864p

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Abstract

Catalytic asymmetric Corey-Chaykovsky epoxidation of broad range of methyl ketones with dimethyloxosulfonium methylide using a complex of La-Li₃-tris(binaphthoxide) (LLB) with a phosphine oxide proceeded smoothly at room temperature, and 2,2-disubstituted terminal epoxides were obtained in high enantioselectivity and excellent yield.

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Key Words

Corey-Chaykovsky Reaction

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ID: J48-Y2008-2120