Lewis acid-catalyzed asymmetric Diels-Alder reactions using chiral sulfoxide ligands: Chiral 2-(arylsulfinylmethyl)-1,3-oxazoline derivatives

Abstract

New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels-Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels-Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction. © 2002 Pharmaceutical Society of Japan.