Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(-)-sparteine system

被引：37

作者：

Tomooka, K ^{[1
]}

Komine, N ^{[1
]}

Sasaki, T ^{[1
]}

Shimizu, H ^{[1
]}

Nakai, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

基金：

日本学术振兴会;

关键词：

carbanions; cyclization; enantiocontrol; lithiation;

D O I：

10.1016/S0040-4039(98)02233-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi /(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9715 / 9718

页数：4

共 16 条

[1]

Bailey W. F., 1994, ADV DETAILED REACTIO, V3, P251

[2] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].