Diastereoselective synthesis of α,α,α′-trisubstituted pyrrolidines and piperidines by directed sequential lithiation/alkylation

被引：7

作者：

Beng, Timothy K. ^{[1
]}

Fox, Nathan ^{[1
]}

机构：

[1] Susquehanna Univ, Dept Chem, Selinsgrove, PA 17870 USA

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 01期

关键词：

Directed lithiation; Trisubstituted pyrrolidines; Trisubstituted piperidines; Diastereoselective alkylation; Electrophilic substitution; CATALYZED ALPHA-ARYLATION; ENANTIOSELECTIVE SYNTHESES; ASYMMETRIC DEPROTONATION; BOC; LITHIATION; CONCISE; 2-ARYLPIPERIDINES; DIASTEREOISOMERS; SUBSTITUTION; EQUIVALENTS;

D O I：

10.1016/j.tetlet.2014.11.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled synthesis of alpha,alpha,alpha'-trisubstituted pyrrolidines and piperidines has been accomplished through alpha'-lithiation/trapping of the corresponding alpha,alpha-disubstituted Boc-protected azaheterocycle with various electrophiles. The relative configuration of the major diastereomer has the alpha'-substituent trans to the alpha-aryl group in the pyrrolidines but cis to the alpha-aryl group in the piperidines. The diastereoselectivity of the lithiation/alkylation of pyrrolidines is unaffected by TMEDA but decreases in the presence of (-)-sparteine in diethyl ether. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：119 / 122

页数：4

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