Lithium Ephedrinate Mediated Aldol Reaction of Arylacetonitriles: Thermodynamic Control of Enantioselectivity

Abstract

Deracemization, the conversion of a racemic mixture into an enantiomerically enriched material, is achieved with the retro-aldol reaction of rac-1 in the presence of lithium (-)-ephedrinate [Eq. (1)]. Remarkably, two stereogenic centers are simultaneously deracemized. This reaction shows that efficient thermodynamic control of the enantioselectivity of aldol reactions is possible.