Synthesis and Resolution of 3,3′-Disubstituted xylBINAP Derivatives and Their Application in Rhodium-Catalyzed Asymmetric Hydrogenation

Abstract

A novel class of 3,3'-disubstituted xylBINAP ligands have been synthesized and tested in the hydrogenations of substituted olefins. This new substitution pattern has demonstrated that the 3,5-dialkyl meta effect and 3,3'-disubstitution can operate in a synergistic fashion in Rh-catalyzed hydrogenation of dehydroamino acids. Notably, (S ax )-8 outperforms BINAP, xylBINAP and previously reported 3,3'-disubstituted BINAP derivatives in the hydrogenation of methyl N-acetamido cinnamate.