Asymmetric Hydrogenation of α,α'-Disubstituted Cycloketones through Dynamic Kinetic Resolution: An Efficient Construction of Chiral Diols with Three Contiguous Stereocenters

摘要

Transition-metal-catalyzed asymmetric hydrogenation is one of the most environmentally benign, atom-efficient, and powerful methods for the synthesis of chiral organic compounds in optically active form. A particularly useful method is the transition-metal-catalyzed asymmetric hydrogenation of configurationally labile substrates through dynamic kinetic resolution (DKR). For example, the hydrogenation of racemic α-substituted ketones catalyzed by chiral ruthenium diphosphine/diamine complexes is a highly efficient method for the one-step preparation of chiral alcohols containing two vicinal stereocenters. However, despite its great potential for the synthesis of chiral compounds such as natural products and biologically active compounds with multiple stereocenters, the asymmetric hydrogenation of racemic α,α'-disubstituted ketones to generate chiral alcohols with three contiguous stereocenters remains a challenge.