ChemInform Abstract: Asymmetric Induction in the Solid State Photochemistry of Salts of Carboxylic Acids with Optically Active Amines.

Abstract

Abstract A general approach to using crystal chirality in asymmetric synthesis is described, It consists of the preparation of crystalline salts of prochiral carboxylic acids with optically active amines followed by photolysis of the salts in the solid state. Conversion of the photoproducts to the corresponding methyl esters by using diazomethane followed by chiral shift reagent NMR analysis revealed enanttomeric excesses ranging from 14–80% depending on the optically active amine employed. In contrast to the solid state results, photolysis of the salts in solution gave only racemic products.