Highly enantio- and diastereoselective tandem generation of cyclopropyl alcohols with up to four contiguous stereocenters

被引：76

作者：

Kim, HY ^{[1
]}

Lurain, AE ^{[1
]}

García-García, P ^{[1
]}

Carroll, PJ ^{[1
]}

Walsh, PJ ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 38期

关键词：

D O I：

10.1021/ja0539239

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation. Route 2 parallels route 1, except that iodoform is used to generate the zinc carbenoid, and the products are iodocyclopropyl alcohols. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation. Copyright © 2005 American Chemical Society.

引用

页码：13138 / 13139

页数：2

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