A method for the kinetic resolution of carbon-oxygen bonds in organocatalytic oxaspirones via hydrogenolysis.

By using asymmetric hydrogenolysis of chiral phosphoric acid catalysts with the Hantzsch ester system, the problem of direct hydrogenolysis of carbon-oxygen bonds in existing technologies has been solved, achieving efficient synthesis of axially chiral biaryl phenolic compounds and centrally chiral oxaspirones, which have high resolution coefficients and pharmaceutical potential.

CN122079942APending Publication Date: 2026-05-26DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
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Patent Information

Application Number
CN202411705149.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-11-26
Publication Date
2026-05-26

AI Technical Summary

Technical Problem

In existing technologies, asymmetric catalytic hydrogenolysis reactions are difficult to synthesize chiral compounds effectively. In particular, there are no reported examples of direct hydrogenolysis of carbon-oxygen bonds in the field of organocatalysis, and the asymmetric synthesis of chiral cannabinols is insufficient, making it difficult to obtain efficient single-configuration products.

Method used

A chiral phosphoric acid catalyst and Hantzsch ester system were used to achieve the kinetic resolution of the carbon-oxygen bond in oxaspirones via asymmetric hydrogenolysis, synthesizing axially chiral biaryl phenolic compounds and centrally chiral oxaspirones. Racemic oxaspirones were used as substrates, and the reaction conditions were mild with a high resolution coefficient.

Benefits of technology

The synthesis of axially chiral biaryl phenolic compounds with high resolution coefficients and centrally chiral oxaspirones was achieved under mild reaction conditions, simple operation, readily available catalysts, and the products have potential medicinal value.

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Abstract

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.
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