Method for synthesizing chiral cyano-containing all-carbon quaternary carbon cyclic compound

By using palladium-catalyzed asymmetric acyloxidation cyclization/acyl migration tandem reaction of alkynyl malononitrile with carboxylic acid, the limitations of limited substrate range and harsh reaction conditions in existing technologies have been overcome, enabling the synthesis of cyano-containing all-carbon quaternary carbon cyclic compounds with high optical purity and high yield.

CN122079943APending Publication Date: 2026-05-26DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
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Patent Information

Application Number
CN202411697099.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-11-25
Publication Date
2026-05-26

AI Technical Summary

Technical Problem

Existing technologies for constructing chiral cyano-containing all-carbon quaternary cyclic compounds suffer from limitations in substrate range and stringent reaction conditions, making it difficult to achieve high optical purity in their synthesis.

Method used

A palladium-catalyzed tandem reaction of alkynyl malononitrile with carboxylic acid involving asymmetric acyl oxidative cyclization/acyl migration was employed. The reaction was carried out using a mixed solvent, oxidant, alkynyl malononitrile compound, carboxylic acid compound, palladium salt, and chiral dinitrogen ligand, and the chiral cyano-containing all-carbon quaternary carbon cyclic compound was obtained by separation.

Benefits of technology

The synthesis of cyano-containing all-carbon quaternary carbon cyclic compounds with high optical purity was achieved, with good yields and a wide substrate range. The operation was simple and the reaction conditions were mild.

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Abstract

The invention discloses a method for synthesizing a chiral cyano-containing all-carbon quaternary carbon cyclic compound, which is characterized by comprising the following steps: mixing a solvent, an oxidant, an alkynyl malononitrile compound, a carboxylic acid compound, a metal palladium salt and a chiral dinitrogen ligand, reacting, drying and separating to obtain the chiral cyano-containing all-carbon quaternary carbon cyclic compound. The asymmetric acylation cyclization / acyl migration cascade reaction of palladium-catalyzed alkynyl malononitrile and carboxylic acid can be realized, and the cyano-containing all-carbon quaternary carbon cyclic compound with optical purity can be obtained with good yield (the ratio of enantiomers can reach 96.5: 3.5). The method has the characteristics of wide substrate range, easiness in preparation of raw materials, simplicity, convenience and practicability in operation, mild reaction conditions and the like.
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