Organocatalyzed Asymmetric Allylic Alkylation of Grignard Reagents

Significance

Practically all known methods for performing asymmetric allylic substitutions involve copper catalysis, and the development of a copper-free protocol would lead to different reactivity and selectivity patterns. The authors developed a new method for the allylic alkylation, based on the activation of organomagnesium reagents by a chiral Lewis base. The products bearing an all-carbon quaternary chiral center were obtained with high enantioselectivity and can be readily transformed into useful enantiopure intermediates such as unnatural amino acids.