A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent

Abstract

A series of α-substituted nitroolefins were employed in organocatalytic asymmetric Michael reactions with aldehydes. γ-Nitro carbonyl products were achieved in good yields (up to 86%) with good stereoselectivities (up to 96% ee and 24 : 1 dr). Reduction of the nitro group followed by intramolecular reductive amination successfully afforded various novel optically active 2,4-disubstituted pyrrolidine compounds.