ENANTIOSELECTIVE BORANE REDUCTION OF ACETOPHENONE CATALYZED BY OXAZABOROLIDINES DERIVED FROM CHIRAL DIETHANOLAMINES

被引：12
|
作者：
DUBOIS, L [1 ]
FIAUD, JC [1 ]
KAGAN, HB [1 ]
机构：
[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,SYNTHESE ASYMETR LAB,CNRS,URA 1497,F-91405 ORSAY,FRANCE
来源：
TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期
关键词：
D O I：
10.1016/0957-4166(95)00134-B
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of oxazaborolidines of types I and 2, derived from chiral diethanolamines and their behaviour, as catalysts for the asymmetric reduction of acetophenone by borane has been investigated. Bicyclic oxazaborolidines of type 2 afforded the expected alcohol in good yield but with modest ee's (ee<40%). Monocyclic oxazaborolidines of type I gave better results. For instance, catalyst Id allowed the isolation of (S) alpha-methyl benzyl alcohol with 72% ee while oxazaborolidine 26, structurally close to 16, produced a remarkable reversal of enantiofacial selectivity. The origin of the enantioselectivity of these catalysts is discussed on the basis of transition slate models.
引用
收藏
页码：1097 / 1104
页数：8
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