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Desymmetrization and Parallel Kinetic Resolution of 1-Ethynylcyclobutanols via Asymmetric Cooperative Gold Catalysis

Ke Zhao, Ziguang Yang, Jielin Yang, Xinyi Li, Carlos D. Quintanilla, Liming Zhang*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93117, United States, Email: zhangchem.ucsb.edu

K. Zhao, Z. Yang, J. Yang, X. Li, C. D. Quintanilla, L. Zhang, J. Am. Chem. Soc., 2023, 145, 27205-27210.

DOI: 10.1021/jacs.3c09288


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Abstract

Gold-ligand cooperation in the presence of a chiral bifunctional phosphine ligand featuring a 3'-phosphine oxide moiety enables a highly enantioselective desymmetrization of 1-ethynylcyclobutanols to provide chiral α-methylenecyclopentanones featuring a diverse array of chiral quaternary and tertiary centers.

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Key Words

cyclopentanones


ID: J48-Y2023