Chiral Sulfoxides as Neutral Coordinate-Organocatalysts in Asymmetric Allylation of N-Acylhydrazones Using Allyltrichlorosilanes

Abstract

Sulfoxides were first introduced to the allylation of N-acylhydrazones with allyltrichlorosilanes as effective neutral coordinate-organocatalysts (NCOs). Both high diastereo- and enantioselectivity were attained when optically active chiral sulfoxides were used. Asymmetric crotylations using (Z)- and (E)-crotyltrichlorosilanes showed a high level of stereospecificity (Z → anti and E → syn) with high enantioselectivity.