Synthesis and application of chiral cis-2,5-disubstituted pyrrolidine organocatalysts

Abstract

The first synthesis of chiral cis-2,5-disubstituted pyrrolidine organocatalysts is described. Their application for the enantioselective Michael addition of nitromethane to α,β-unsaturated aldehydes with excellent yield (up to 91%) and enantioselectivity (up to >99% ee) is demonstrated. Another catalytic application for the reaction of 2,4-hexadienal with nitrostyrene is also showcased.