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Synthesis 2021; 53(10): 1771-1784
DOI: 10.1055/s-0040-1706101
DOI: 10.1055/s-0040-1706101
paper
Synthesis of sp3-Enriched β-Fluoro Sulfonyl Chlorides
The work was funded by Enamine Ltd. Additional funding from the Ministry of Education and Science of Ukraine, Grant No. 19BF037-03 (A.V.D. and O.O.G.) is also acknowledged.
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 blocksSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706101.
- Supporting Information
Publication History
Received: 29 October 2020
Accepted after revision: 13 November 2020
Article published online:
15 December 2020
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