Theoretical Model for the Stereoselectivity and Solvent Dependence of an Enantioselective Amine N-acetylation

Quantum mechanical studies of a stereoselective amine N-acetylation have led to a rationalization of the origins of stereoselective. The alternation of selectivity by polar solvents is found to result from a reduction of intramolecular hydrogen-bonding and a change in of the most stable diastereoisomeric intermediate.