Organocatalytic Michael Addition of β-Ketoesters and Ethenesulfonyl Fluoride: Access to Chiral δ-Sultones via SuFEx Chemistry

Abstract

Sultones have been gaining popularity within medicinal chemistry due to their vast biological activity; however, access to chiral δ-sultones remains limited. In this study, we have developed an organocatalyzed Michael addition reaction between β-ketoesters and ethenesulfonyl fluoride using a bifunctional thiourea catalyst. This methodology resulted in 11 Michael adducts in yields up to 99% and enantioselectivities up to 84%. Subsequent cyclization under sulfonyl fluoride exchange conditions afforded seven novel chiral δ-sultones in low to moderate yields, generally preserving the enantioselectivity. This work presents an innovative strategy for efficiently synthesizing chiral δ-sultones.

Keywords

Organocatalysis - Michael addition - SuFEx - Sultones - Beta-ketoesters

Publikationsverlauf

Eingereicht: 12. August 2025

Angenommen nach Revision: 28. November 2025

Artikel online veröffentlicht:
09. Dezember 2025

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