Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O):: Application of α,β-unsaturated N-acyl pyrroles as ester surrogates

被引：81

作者：

Kinoshita, T ^{[1
]}

Okada, S ^{[1
]}

Park, SR ^{[1
]}

Matsunaga, S ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 38期

关键词：

asymmetric catalysis; epoxiclation; samarium; synthetic; methods; Wittig reactions;

D O I：

10.1002/anie.200352509

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Waste not, want not: Efficient one-pot access to optically active epoxides with 96 to 99.5% ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by-product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N-acyl pyrrole Wittig product (see scheme). The N-acyl pyrrole functionality is key to the high reactivity and selectivity observed. R = alkyl, aryl, vinyl.

引用

页码：4680 / 4684

页数：5

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