Selective synthesis of functionalized α,β-multi-substituted α-amino cyclopentanones via an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles

Abstract

An efficient approach to construct α-amino cyclopentanones bearing consecutive quaternary and ternary carbon centers is described through an α-iminol rearrangement enabled by Pd-catalyzed addition of arylboronic acids to nitriles. Various α,β-multi-substituted α-amino cyclopentanones can be prepared in good to high yields under mild reaction conditions. This transformation features excellent regio-selectivity, stereospecificity, high step-economy and synthetic diversity, and offers a new protocol to prepare high-value added compounds through Pd-catalyzed addition of boronic acids to nitriles in a selective manner.