Chiral sulfoxide-olefin ligands: tunable stereoselectivity in Rh-catalyzed asymmetric 1,4-additions

A class of chiral sulfoxide-olefins were designed and synthesized through concise routes. Their applications as ligands in Hayashi-Miyaura reaction were studied, which found that vinyl substituents of the ligands vary in stereocontrolling ability. Particularly, either isomer of adducts with excellent ees could be readily obtained through changing the position of the substituents of olefins as well as changing the configuration of the C=C bond of the ligands. Meanwhile, the substrate scope of arylboronic acids and alkenes was clearly shown. (C) 2012 Elsevier Ltd. All rights reserved