Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement

被引：16

作者：

Huang, Nianyu ^{[2
]}

Liao, Hongze ^{[1
]}

Yao, Hui ^{[1
]}

Xie, Tianpeng ^{[2
]}

Zhang, Shasha ^{[1
]}

Zou, Kun ^{[2
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, 21 Nanyang Link, Singapore 637371, Singapore

[2] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

GOLD-CATALYZED REARRANGEMENT; PROPARGYLIC ESTERS; ORTHO-ALKYNYLBENZOATES; FERRIER REARRANGEMENT; THIOGLYCOSIDE DONORS; MECHANISTIC INSIGHTS; O-GLYCOSYLATION; ACTIVATION; ACETATES; CYCLOISOMERIZATION;

D O I：

10.1021/acs.orglett.7b03062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel gold-catalyzed C-glycosylation has been developed to gain access to alpha,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement of allenic ester as the glycosyl acceptor. A wide range of substrate scope with good to excellent yields was achieved with complete diastereoselectivity.

引用

页码：16 / 19

页数：4

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