Synthesis of Optically Active Aliphatic Nitriles from Aldehydes and Acids

Abstract

Optically active nitriles are very useful starting products for the preparation of chiral amines¹, ketones² and pyridines³. They are usually accessible from the corresponding acids via amide dehydration⁴, through nucleophilic substitution of suitable leaving groups by he CN⁻ anion⁵ and by dehydration of aldomixes³. However, the preparation of optically active nitrils with the asymmetric center in the -a- position with respect to the functional group and with high optical purity presents some difficulties due to the possible racemization of the chiral center in the starting compound used for the its preaparation and in the reaction products themselves^4,6