Cascade Michael/aldol/rearrangement between phenacylmalononitriles and maleimides: highly diastereoselective access to functionalized bicyclic cyclopentenes containing a CN-substituted all-carbon quaternary center

Abstract

Annulation of phenacylmalononitriles with maleimides offers a highly diastereoselective synthesis of unprecedented multifunctionalized bicyclic cyclopentenes containing a CN-substituted all-carbon quaternary center. Experimental and theoretical studies revealed that the reaction likely involves a Michael/aldol/rearrangement sequence in a domino manner.