Stereoselective Palladium-Catalyzed Alkenylation and Alkynylation of Thioglycosides

被引：49

作者：

Brachet, Etienne ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

Messaoudi, Samir ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, BioCIS UMR 8076, LabEx LERMIT,Lab Chim Therapeut,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 13期

关键词：

beta-alkenylthioglycosides; beta-alkynylthioglycosides; palladium catalysis; thioglycosides; COUPLING REACTIONS; ARYL CHLORIDES; THIOLS; THIOOLIGOSACCHARIDES; CONVENIENT; INHIBITORS; REDUCTION; SULFIDES; HALIDES; ACCESS;

D O I：

10.1002/adsc.201300419

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient and unprecedented palladium-catalyzed S-glycosylation reaction of a range of alkenyl and alkynyl halides by using thiosugars as nucleophile partners has been established. With palladium diacetate in combination with Xantphos as the catalytic system, a variety of beta-alkenylthioglycosides as well as beta-alkynylthioglycosides can be prepared in good to excellent yields. The efficiency of this general protocol was well-demonstrated by the formal synthesis of a leaf-closure beta-glucosidase inhibitor.

引用

收藏

页码：2627 / 2636

页数：10

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