Ring-opening metathesis-cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes

被引：31

作者：

Mayo, P ^{[1
]}

Tam, W ^{[1
]}

机构：

[1] Univ Guelph, Dept Chem & Biochem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

TETRAHEDRON | 2002年 / 58卷 / 47期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ring-opening metathesis; cross-metathesis; ruthenium catalyst; carbene; chemoselectivity; regioselectivity; remote substituent affect;

D O I：

10.1016/S0040-4020(02)01276-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring-opening metathesis-cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes were investigated. The reactions with symmetrical 2,3-disubstituted norbornadienes were found to be highly chemoselective, with the ROM reactions occurring only on the less substituted or less sterically hindered double bonds regardless of the electronic nature of the substituents, giving highly substituted cyclopentenes in moderate to good yields. This study provides an efficient method for the stereoselective synthesis of highly substituted cyclopentenoids. Long-range electronic effect of a remote substituent on unsymmetrical norbornenes in the ROM-CM reactions was also investigated. Low levels of regioselectivities were observed (50:50 to 69:31) with various remote substituents on the norbomenes. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9513 / 9525

页数：13

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