Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines

被引：9
|
作者：
Gawley, RE [1 ]
Barolli, G
Madan, S
Saverin, M
O'Connor, S
机构：
[1] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA
[2] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
(stannanyl)pyrrolidines; TCC; N-acyliminium ion; asymmetric synthesis;
D O I：
10.1016/j.tetlet.2003.12.080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1759 / 1761
页数：3
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