An Asymmetric Biaryl Suzuki Cross-Coupling Reaction: Stereogenic Benzylic Carbinols as Chiral Auxiliaries

✍ Scribed by Pierre-Emmanuel Broutin; Françoise Colobert

• Book ID: 102178224
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 321 KB
• Volume: 2005
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400638

✦ Synopsis

Abstract

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 β‐keto sulfoxide. In the presence of Pd(OAc)~2~/CsF and dppf or PPh~3~ excellent yields and atropodiastereoselectivities were obtained. The absolute configurations of the biaryls were determined by X‐ray crystallography and ^1^H NMR NOESY experiments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)