Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors

被引：22

作者：

Matsunaga, Shigeki ^{[1
]}

Qin, Hongbo ^{[1
]}

Sugita, Mari ^{[1
]}

Okada, Shigemitsu ^{[1
]}

Kinoshita, Tomofumi ^{[1
]}

Yamagiwa, Noriyuki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2006年 / 62卷 / 28期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/j.tet.2005.12.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric epoxidation of alpha,beta-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm(O-i-Pr)(3)/(R)-H-8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiornefic excess (up to > 99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2-0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of oc, -unsaturated N-acylpyrroles are also described. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6630 / 6639

页数：10

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