Synthesis of sp³-Enriched β-Fluoro Sulfonyl Chlorides

Abstract

A three-step approach to the synthesis of sp³-enriched β-fluoro sulfonyl chlorides starting from alkenes is reported. The method was successfully applied to a wide range of acyclic and cyclic substrates, bearing either an exocyclic or an endocyclic double bond. The procedure worked with a wide range of substrates and tolerated a number of functional and protecting groups. Moreover, the target cyclic compounds were obtained as single cis diastereomers on a multigram scale. The title compounds are promising building blocks for drug discovery that can be used to obtain sp³-enriched β-fluoro and α,β-unsaturated sulfonamides.

Key words

organosulfur compounds - organofluorine compounds - oxidation­ - sulfonyl chlorides - building blocks

Publikationsverlauf

Eingereicht: 29. Oktober 2020

Angenommen nach Revision: 13. November 2020

Artikel online veröffentlicht:
15. Dezember 2020

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