Synthesis of stereoselectively labelled citric acids transformable into chiral acetic acids

Abstract

The ketones (1b) and (1c) have been transformed into the monodeuteriated citric acids, (4b) and (4c) respectively, which are suitable starting materials for the synthesis of chiral acetic acids and other labelled compounds; under base catalysis, the axial 2-H in (1a) exchanges with deuterium more than 1000 times faster than the axial 2-H in 4-t-butylcyclohexanone.