Cyclisation of acetylenic carboxylic acids and acetylenic alcohols to oxygen-containing heterocycles using cationic rhodium(I) complexes

被引：92

作者：

Elgafi, S

Field, LD ^{[1
]}

Messerle, BA

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

[2] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2000年 / 607卷 / 1-2期

基金：

澳大利亚研究理事会;

关键词：

rhodium; carbonyl; cationic; catalysts; cyclisation of alkynoic acids;

D O I：

10.1016/S0022-328X(00)00233-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Square planar cationic rhodium(I) dicarbonyl complexes [{Rh((mim)(2)CH2)(CO)(2)}+BPh4-] (1) and [{Rh((mBnzim)(2)CH2)(CO)(2)}+BPh4-] (2) [mim =N-methylimidazol-2-yl, mBnzim = N-methylbenzimidazol-2-yl] are catalysts for the cyclisation of alkynoic acids to lactones. The unsaturated acids, 4-pentynoic acid, 4-hexynoic acid and 5-hexynoic acid were cyclised to gamma-methylene-gamma-butyrolactone, E-5-ethylidenetetrahydro-2-furanone and 6-methylidenetetrahydo-2-pyrone, respectively. Cyclisation of 4-hexynoic acid proceeds stereoselectively with exclusive formation of the E-isomer of 5-ethylidenetetrahydro-2-furanone. Complexes 1 and 2 also catalyse cyclisation of acetylenic alcohols to oxygen-containing heterocycles. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：97 / 104

页数：8

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