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

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).