Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers

被引：97

作者：

Gao, Lizhu ^{[3
]}

Hwang, Geum-Sook ^{[1
,2
]}

Ryu, Do Hyun ^{[3
]}

机构：

[1] Chungnam Natl Univ, Korea Basic Sci Inst, Seoul 136713, South Korea

[2] Chungnam Natl Univ, Grad Sch Analyt Sci & Technol, Seoul 136713, South Korea

[3] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 51期

关键词：

ASYMMETRIC CYCLOPROPANATION; STEREOSELECTIVE CYCLOPROPANATION; DIAZO REAGENTS; CONSTRUCTION; ALKENES; DERIVATIVES; CARBON; ACID; ALKYLATION;

D O I：

10.1021/ja209270e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of alpha-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation 1b as a catalyst, the reaction proceeded in high yield (up to 93%) with high to excellent diastereoselectivity (up to 98% de) and enantio-selectivity (up to 95% ee).

引用

页码：20708 / 20711

页数：4

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