Catalytic Asymmetric Construction of Quaternary Stereocenters through Rhodium-Catalyzed Addition of Organoboronic Acids

摘要

Enantioselective construction of quaternary carbon stereocenters is an important, but challenging, objective in organic chemistry. 1,4-Addition of carbon-nucleophiles to beta,beta-disubstituted alpha,beta-unsaturated compounds is potentially a useful strategy for efficient assembly of this type of molecular skeleton. It is. therefore, of high value to achieve such a transformation in a catalytic asymmetric fashion. Herein we describe the development of a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to 3-substituted maleimides 1 , furnishing 3,3-disubstituted succinimides 2 in high regio- and enantioselectivity (eq 1).