This invention discloses a method for the
kinetic resolution of oxaspirone via organocatalytic
hydrogenolysis. Using chiral
phosphate CPA as a catalyst, Hantzsch ester as a
hydrogen source, and racemic oxaspirone 2,4-dien-6-one rac-1 as a substrate, a series of axially chiral biaryl phenolic compounds 2 are synthesized via asymmetric
hydrogenolysis, and the central chiral oxaspirone 1 is recovered. This invention offers advantages such as simple and practical operation, readily available raw materials,
high resolution coefficient, and good enantioselectivity. Some of the axially chiral biaryl products have structures similar to axially chiral
cannabinol, possessing potential medicinal value.