Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent π-Interactions.

ABSTRACT

While Sharpless asymmetric dihydroxylation is widely utilized to convert various alkenes into diols with excellent enantioselectivies, kinetic resolution by means of this fundamental catalysis has generally proven to be ineffective. Here we report that, by relying on noncovalent π-interactions that purposely include the substrate's stereocenter in the corresponding catalyst-substrate interaction framework, AD-based kinetic resolution of allylic amides is realized. This method enables such versatile chiral building blocks to be easily accessed with excellent enantiomeric excesses (ee's).