Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


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.

see article for more examples



Key Words

Corey-Chaykovsky Reaction


ID: J48-Y2008-2120