The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanols

The reaction between racemic acyl chlorides and racemic trans-2-substituted-cyclohexanols proceeds diastereoselectively. We found for the first time that addition of a tertiary amine not only accelerates the acylation, but for some substituents leads to complete inversion of diastereoselectivity. These observations have been rationalized in terms of a possible stereoselective intramolecular assistance by the substituent group during the acylation of the neighboring hydroxyl group