Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides

Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin

doi:10.1016/j.isci.2019.10.051

Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides

iScience. 2019 Nov 22:21:695-705. doi: 10.1016/j.isci.2019.10.051. Epub 2019 Oct 30.

Authors

Balakrishna Moku¹, Wan-Yin Fang¹, Jing Leng¹, Linxian Li², Gao-Feng Zha³, K P Rakesh¹, Hua-Li Qin⁴

Affiliations

¹ State Key Laboratory of Silicate Materials for Architectures, and School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, P. R. China.
² Ming Wai Lau Centre for Reparative Medicine, Karolinska Institute, Hong Kong, China.
³ State Key Laboratory of Silicate Materials for Architectures, and School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, P. R. China; Ming Wai Lau Centre for Reparative Medicine, Karolinska Institute, Hong Kong, China.
⁴ State Key Laboratory of Silicate Materials for Architectures, and School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, P. R. China. Electronic address: qinhuali@whut.edu.cn.

Abstract

Rh-catalyzed, highly enantioselective (up to 99.8% ee) synthesis of aliphatic sulfonyl fluorides was accomplished. This protocol provides a portal to a class of novel 2-aryl substituted chiral sulfonyl fluorides, which are otherwise extremely difficult to access. This asymmetric synthesis has the feature of mild conditions, excellent functional group compatibility, and wide substrate scope (51 examples) generating a wide array of structurally unique chiral β-arylated sulfonyl fluorides for sulfur(VI) fluoride exchange (SuFEx) click reaction and drug discovery.

Keywords: Catalysis; Organic Chemistry; Stereochemistry.