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,
wzheng
nju.edu.cn
S. Yuan, W.-H. Zheng, J. Org. Chem., 2022, 87, 713-720.
DOI: 10.1021/acs.joc.1c02710
see article for more reactions
Abstract
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.
see article for more examples
proposed reaction pathway
Key Words
propargyl fluorides, α-fluoroesters, NFSI, organocatalysis
ID: J42-Y2022
