Diels-Alder reactivity of a ketovinylphosphonate with cyclopentadiene and furan.

被引:27
|
作者
McClure, CK [1 ]
Hansen, KB [1 ]
机构
[1] UNIV DELAWARE, DEPT CHEM & BIOCHEM, NEWARK, DE 19716 USA
关键词
D O I
10.1016/0040-4039(96)00235-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Diels-Alder reactions between diethyl ketovinylphosphonate 5 and cyclopentadiene or furan were performed with and without Lewis acid assistance. The acetyl group directed endo in all cases, with ratios varying from 1.4:1 - 6.7:1 (acetyl endo).
引用
收藏
页码:2149 / 2152
页数:4
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