An asymmetric biaryl Suzuki cross-coupling reaction: Stereogenic benzylic carbinols as chiral auxiliaries

被引：27

作者：

Broutin, PE ^{[1
]}

Colobert, F ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Stereochim Associe, F-67087 Strasbourg, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 06期

关键词：

asymmetric synthesis; cross-coupling; palladium; Suzuki reaction; stereogenic carbinol; sulfoxides;

D O I：

10.1002/ejoc.200400638

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric biaryl Suzuki coupling reactions were performed with various aryl- or naphthylhalide-bearing enantiomerically pure benzylic alcohols and aryl- or naphthylboronic acids (or esters). The stereogenic benzylic alcohol was introduced by diastereoselective reduction of the arylhalide bearing a beta-keto sulfoxide. In the presence of Pd(OAC)(2)/CsF and dppf or PPh3 excellent yields and atropodiastereoselectivities were obtained. The absolute configurations of the biaryls were determined by X-ray crystallography and H-1 NMR NOESY experiments. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：1113 / 1128

页数：16