Catalytic asymmetric synthesis of 2,2-disubstituted terminal epoxides via dimethyloxosulfonium methylide addition to ketones

被引：78

作者：

Sone, Toshihiko ^{[1
]}

Yamaguchi, Akitake ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 31期

关键词：

D O I：

10.1021/ja803864p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric Corey-Chaykovsky epoxidation of ketones with dimethyloxosulfonium methylide 2 using an LLB 1a + Ar3P = O complex proceeded smoothly at room temperature, and 2,2-disubstituted termimal epoxides were obtained in high enantioselectivity (91-97%) and yield (> 88-99%) from a broad range of methyl ketones with 1-5 mol % catalyst loading. The use of achiral addictive Ar3P = O 5i was important to achieve high enantioselectivity.

引用

页码：10078 / +

页数：3

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