A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to alpha,beta-unsaturated ketones: Synthesis of (-)-(R)-phenyl 2-phenylpropyl ketone

被引:13
作者
Bratovanov, S [1 ]
Bienz, S [1 ]
机构
[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND
关键词
D O I
10.1016/S0957-4166(97)00134-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with alpha-silylated alpha,beta-unsaturated ketones afforded the respective addition products with pi-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1587 / 1603
页数:17
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