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

Xiang-Feng Tao; Hua-Li Qin

doi:10.1055/s-0041-1738449

Synthesis, Table of Contents

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∗

Abstract

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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.

Key words

α,β-unsaturated γ-amino sulfonyl fluorides - allylic amines - vinyl sulfonyl fluorides - click chemistry - covalent inhibitors

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