FIRST EXAMPLE OF REVERSAL OF NORMAL STEREOSELECTIVITY IN THE INTRAMOLECULAR PAUSON-KHAND REACTION

被引：27

作者：

CASALNUOVO, JA ^{[1
]}

SCOTT, RW ^{[1
]}

HARWOOD, EA ^{[1
]}

SCHORE, NE ^{[1
]}

机构：

[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 08期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(94)88010-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselectivity favoring exo substituent orientation in the intramolecular Pauson-Khand reaction of 3-methyl-4-hydroxy-1,6-heptenynes to form bicyclo[3.3.0]octenones is affected by the relative stereochemistry at C3 and C4. Cycloaddition of one stereoisomer of 3,5-dimethyl-4-propargyl-1,6-heptadiene gives predominantly the bicyclo[3.3.0]octenone isomer containing both substituents in more hindered endo orientations. An explanation based upon the effect of conformational preferences prior to metallacycle formation is proposed.

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页码：1153 / 1156

页数：4

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