STEREOSELECTIVE HYDRIDE REDUCTIONS OF CYCLIC N-DIPHENYLPHOSPHINYL IMINES - HIGHLY DIASTEREOSELECTIVE SYNTHESES OF PROTECTED PRIMARY AMINES

被引:27
作者
HUTCHINS, RO
ADAMS, J
RUTLEDGE, MC
机构
[1] Department of Chemistry, Drexel University, Philadelphia
关键词
D O I
10.1021/jo00128a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.
引用
收藏
页码:7396 / 7405
页数:10
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