[4+3]CYCLOADDITIONS OF CYCLIC OXYALLYLS AND CYCLIC 1,3-DIENES

被引：42

作者：

JIN, SJ ^{[1
]}

CHOI, JR ^{[1
]}

OH, JH ^{[1
]}

LEE, DH ^{[1
]}

CHA, JK ^{[1
]}

机构：

[1] UNIV ALABAMA,DEPT CHEM,TUSCALOOSA,AL 35487

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 44期

关键词：

D O I：

10.1021/ja00149a014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The [4 + 3] cycloaddition of the oxyallyl intermediates, derived from 2-chlorocyclohexanone and related compounds, to cyclic 1,3-dienes under the Fohlisch conditions (Et(3)N in CF3CH2OH) has been examined to assess its scope and limitations. Effects of substitution with alkyl or alkoxy groups on the cyclohexanone ring, along with variations of the base, solvent, or ring size have been investigated. Also included is a comparison between the Fohlisch cycloaddition and the Schmid cycloaddition (utilizing alpha'-chloroenamines). These reactions of cyclic oxyallyls afford tricyclic or tetracyclic cycloadducts of considerable molecular complexity with a well-defined stereochemical outcome and, thus, represent a new synthetic route to functionalized medium-sized carbocycles and heterocycles.

引用

页码：10914 / 10921

页数：8

共 54 条

[1] FAVORSKII REARRANGEMENTS .9. STEREOCHEMISTRY OF REACTION WITH 2-BROMO-4-METHYL-4-PHENYLCYCLOHEXANONE [J].