Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes

被引:19
作者
Ramachandran, PV [1 ]
Xu, WC [1 ]
Brown, HC [1 ]
机构
[1] PURDUE UNIV, HC BROWN & RB WETHERILL LABS CHEM, W LAFAYETTE, IN 47907 USA
关键词
D O I
10.1016/0040-4039(96)00969-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of the diisopinocampheylborinates of a representative series of methyl ketones with a representative series of aldehydes, both of differing steric requirements provides aldols whose enantiomeric purities depend on the steric requirements of both the ketones and the aldehydes. This study has shown that increasing the steric requirements of the R group in the ketones has a pernicious effect on the ee, while increasing the steric requirements of the R group in the aldehydes exerts a beneficial effect on the ee. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:4911 / 4914
页数:4
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