PI-FACIAL DIASTEREOSELECTIVITY IN THE DIELS-ALDER REACTIONS OF CIS-CYCLOHEXA-3,5-DIENE-1,2-DIOL AND DERIVATIVES WITH N-PHENYLMALEIMIDE

被引：18

作者：

GILLARD, JR ^{[1
]}

BURNELL, DJ ^{[1
]}

机构：

[1] MEM UNIV NEWFOUNDLAND,DEPT CHEM,ST JOHNS A1B 3X7,NEWFOUNDLAND,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 05期

关键词：

D O I：

10.1139/v92-167

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Phenylmaleimide undergoes Diels-Alder cycloaddition predominantly to the face of cis-cyclohexa-3,5-diene-1,2-diol (3) syn to the oxygen functions. Derivatization can be used to alter the pi-facial diastereoselectivity in a synthetically useful manner. The best cases are the exclusive, high yield, production of the syn-addition product with the trimethylsilyl ether derivative (8), and the exo-benzylidine derivative (26) gave a 96:4 anti/syn ratio of adducts.

引用

页码：1296 / 1307

页数：12

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