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Enantioselective Construction of Tertiary α-Alkyl Fluoride via BTM-Catalyzed Fluorination of α-Alkynyl-Substituted Acetic Acids

Shiru Yuan and Wen-Hua Zheng*

*School of Chemistry and Chemical Engineering, Nanjing University, 163 Xianlin Avenue, Nanjing, Jiangsu 210023, China,

S. Yuan, W.-H. Zheng, J. Org. Chem., 2022, 87, 713-720.

DOI: 10.1021/acs.joc.1c02710

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An isothiourea-catalyzed fluorination of alkynyl-substituted acetic acids provides a broad range of optically active tertiary α-alkyl fluorides in high enantioselectivity (up to 97% ee). Furthermore, this methodology can be scaled up to a Gram scale without loss of enantioselectivity.

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proposed reaction pathway

Key Words

propargyl fluorides, α-fluoroesters, NFSI, organocatalysis

ID: J42-Y2022