Can an aromatic ring alter the reactions of a nearby unsaturated imide? A study of the rate and selectivity of nitrile oxide cycloaddition reactions of acryloyl derivatives of the Rebek imide benzoxazole

被引:22
作者
Curran, DP
Yoon, MH
机构
[1] Department of Chemistry, University of Pittsburgh, Pittsburgh
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4020(96)01167-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloadditions of acryloyl derivatives of the Rebek imide benzoxazole are extraordinarily stereoselective, but have rates and regioselectivities that otherwise parallel those of a simple achiral model. It appears that the benzoxazole ring of these compounds completely shields the inner face of the nearby alkene, but has no measurable effect on the rate of reactions on the outer face. (C) 1997, Elsevier Science Ltd.
引用
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页码:1971 / 1982
页数:12
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