ALLYLIC ALCOHOLS OF UNEXPECTED CONFIGURATION BY OXAZABOROLIDINE-CATALYZED REDUCTION OF ALPHA,BETA-UNSATURATED KETONES - AN EXPLANATION-BASED ON MO CALCULATIONS

被引：29

作者：

BACH, J ^{[1
]}

BERENGUER, R ^{[1
]}

FARRAS, J ^{[1
]}

GARCIA, J ^{[1
]}

MESEGUER, J ^{[1
]}

VILARRASA, J ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,DIV 3,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 11期

关键词：

D O I：

10.1016/0957-4166(95)00357-U

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

While the reduction of most alpha,beta-unsaturated ketones with BH3:SMe(2) in the presence of (R)B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine [(R)-2] affords allylic alcohols of the S configuration, that of alpha,beta-unsaturated ketones branched at both the alpha and alpha' positions gives alcohols of the R configuration. Theoretical calculations on complexes of representative enones with BH3 (6-31G*) or with BH3:(R)-2 (AMI) may account for the apparent changes in the steric requirements on either side of the CO group.

引用

页码：2683 / 2686

页数：4

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