Stereoselective C-Glycosylation Reactions with Arylzinc Reagents

被引：114

作者：

Lemaire, Sebastien ^{[1
]}

Houpis, Ioannis N. ^{[1
]}

Xiao, Tingting ^{[3
]}

Li, Juanjuan ^{[3
]}

Digard, Eric ^{[1
]}

Gozlan, Charlotte ^{[1
]}

Liu, Renmao ^{[3
]}

Gavryushin, Andrey ^{[2
]}

Diene, Coura ^{[2
]}

Wang, Youchu ^{[3
]}

Farina, Vittorio ^{[1
]}

Knochel, Paul ^{[2
]}

机构：

[1] Janssen Pharmaceut, Pharmaceut Dev & Mfg Sci, B-2340 Beerse, Belgium

[2] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

[3] WuxiApptec, Proc Chem, Shanghai 200131, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 06期

关键词：

CROSS-COUPLING APPROACH; ATE COMPLEXES; GLYCOSIDES; TRIALKYLMANGANATE; DISCOVERY; INHIBITOR; ALKYL;

D O I：

10.1021/ol300220p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, transition-metal-free, highly stereoselective cross-coupling reaction between glycosyl bromides and various arylzinc reagents leading to beta-arylated glycosides is reported. The stereoselectivity of the reaction is explained by invoking anchimeric assistance via a bicyclic intermediate. Stereochemical probes confirm the participation of the 2-pivaloyloxy group. Finally, this new method was applied to a short and efficient stereoselective synthesis of Dapagliflozin and Canagliflozin.

引用

页码：1480 / 1483

页数：4

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