SEARCH FOR CONFIGURATIONALLY STABLE, ARACEMIC ALPHA-AMINO ORGANOLITHIUMS

被引:70
作者
GAWLEY, RE
ZHANG, QH
机构
[1] Department of Chemistry, University of Miami, Coral Gables
关键词
ALPHA-AMINO ORGANOLITHIUMS; ALPHA-AMINO CARBANIONS; 2-LITHIOPIPERIDINE; 2-LITHIOPYRROLIDINE; CONFIGURATIONALLY STABLE CARBANIONS;
D O I
10.1016/S0040-4020(01)90459-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The search for configurationally stable alpha-amino carbanions has led to an interesting observation of differing reactivity of diastereomeric organolithiums and to the characterization of aracemic 2-lithio-N-methylpiperidine and 2-lithio-N-methylpyrrolidine as configurationally stable alpha-aminoorganolithiums. Details for the preparation of these and related alpha-lithioheterocycles, evaluation of their chemical and configurational stability, and a preliminary evaluation of the stereoselectivity of their reactions with electrophiles is presented.
引用
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页码:6077 / 6088
页数:12
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