Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β‑Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions

The
enantioselective kinetic resolution of β-unfunctionalized
primary alcohols with benzoyl chloride was carried out in the presence
of a catalytic amount of a novel chiral 1,2-diamine derived from (S)-proline. Several valuable chiral 2-substituted propan-1-ols
were obtained with good enantioselectivities. Density functional theory
calculations revealed that the noncovalent interaction, such as CH−π
interaction, is crucial for the enantioselectivity of the resolution.
This study was conducted through an interplay between experiment and
computation.