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
收藏
页码：6336 / 6339
页数：4
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