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

页码：1759 / 1761

页数：3

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