Phosphine-Free Suzuki-Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

被引：65

作者：

Cobo, Isidro ^{[1
,2
]}

Matheu, M. Isabel ^{[2
]}

Castillon, Sergio ^{[2
]}

Boutureira, Omar ^{[1
,2
]}

Davis, Benjamin G. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 07期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

C-GLYCOSIDE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ARYL GLYCOSIDES; GLYCOSYLTRANSFERASE INHIBITORS; CARBOHYDRATE-CHEMISTRY; PERACETYLATED GLYCALS; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; EXO-GLYCALS;

D O I：

10.1021/ol3003139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.

引用

页码：1728 / 1731

页数：4

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