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
收藏
页码：119 / 122
页数：4
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