Rhodium/olefin-catalyzed reaction of arylboronic acids with an α-acetamido acrylic ester: Mizoroki-Heck-type reaction versus asymmetric conjugate addition

In this paper we present our results concerning the rhodium/olefin-catalyzed reaction of arylboronic acids with an α-acetamido acrylic ester. With a chiral norbornadiene ligand rather low enantioselectivities (up to 21% ee) were obtained. Besides the expected conjugate adduct, we also observed the formation of a significant amount of Mizoroki-Heck-type product. The ratio of the conjugate adduct/Mizoroki-Heck product could be adjusted by a proper choice of the olefin ligand.