The asymmetric Horner-Emmons reaction using a benzopyrano-isoxazolidine auxiliary

被引:54
作者
Abiko, A [1 ]
Masamune, S [1 ]
机构
[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)02352-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric Horner-Emmons reaction of the phosphonate derived from a chiral benzopyrano-isoxazolidine (with 4-substituted cyclohexanones) proceeded in high diastereoselectivity with the aid of KHMDS and 18-crown-6 ether. Enantiomerically pure, axially dissymmetric cyclohexylidene alcohols, aldehydes and ketones were obtained from the diastereomerically pure Homer-Emmons products in a single step.
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页码:1077 / 1080
页数:4
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