Synthesis 2023; 55(20): 3373-3381
DOI: 10.1055/s-0041-1738449
paper

A General Protocol for the Chemo- and Stereoselective Construction of α,β-Unsaturated γ-Amino Sulfonyl Fluorides

Xiang-Feng Tao
,
Hua-Li Qin
We are grateful to the National Natural Science Foundation of China (Grant No. 22071190) and Wuhan University of Technology for financial support.


Abstract

A general protocol for the simple, efficient, and mild synthesis of α,β-unsaturated γ-amino sulfonyl fluorides is developed via a base-catalyzed N-alkylation reaction of aromatic amines with (E)-3-bromoprop-1-ene-1-sulfonyl fluoride. This transformation exhibits excellent chemo- and stereoselectivity, mild conditions, broad functional group compatibility and operational simplicity, making it a potentially valuable procedure in medicinal chemistry, chemical biology, and drug discovery.

Supporting Information



Publikationsverlauf

Eingereicht: 19. Mai 2023

Angenommen nach Revision: 28. Juni 2023

Artikel online veröffentlicht:
15. August 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany