Gold(I)-catalyzed reactions: substituents-dependent selective formation of bisfurans and 1,3-diketones from 1-allkynyl-2,3-epoxy alcohols

被引：25

作者：

Dai, Lun-Zhi ^{[1
]}

Shi, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 45期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetlet.2008.08.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild access to bisfurans and 1,3-diketones via gold(I)-catalyzed transformation of 1-alkynyl-2,3-epoxy alcohols 1 has been described. The formation of bisfurans 2 is proposed to proceed through the sequential formation of 2-hydroxymethylfuran, followed by self-condensation in the presence of gold complex. Whereas the formation of 1,3-diketones 3 is resulted from a domino C-C bond cleavage of epoxide system with the assistance of hydroxyl group and subsequent hydrolysis. Substituents on the oxirane have a significant effect on the selective formation of the two kinds of products. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6437 / 6439

页数：3

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