Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes

被引：30

作者：

Hosseyni, Seyedmorteza ^{[1
]}

Smith, Courtney A. ^{[1
]}

Shi, Xiaodong ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, 4202 East Fowler Ave, Tampa, FL 33620 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 24期

基金：

美国国家科学基金会;

关键词：

STEREOSELECTIVE-SYNTHESIS; 2+2 CYCLOADDITION; TERMINAL ALKYNES; PROPARGYLIC ALCOHOLS; UNACTIVATED ALKYNES; GLYCOSYL DONORS; C-GLYCOSIDES; CYCLOISOMERIZATION; POLYMERIZATION; ALKYNYLATION;

D O I：

10.1021/acs.orglett.6b03228

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity.

引用

页码：6336 / 6339

页数：4

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