Gold-catalysed cyclic ether formation from diols

被引：23

作者：

Jiang, Xiaolu ^{[1
]}

London, Emma K. ^{[1
]}

Morris, David J. ^{[1
]}

Clarkson, Guy J. ^{[1
]}

Wills, Martin ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

TETRAHEDRON | 2010年 / 66卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

Gold; Catalysis; Cyclisation; Diol; Ether; TRANSFER HYDROGENATION; ACIDS; STEREOCHEMISTRY; ETHERIFICATION; OPPORTUNITIES; BENZYLATION; REDUCTION; ALCOHOLS;

D O I：

10.1016/j.tet.2010.10.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an S(N)1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：9828 / 9834

页数：7

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