Synthesis 2021; 53(10): 1771-1784
DOI: 10.1055/s-0040-1706101
paper

Synthesis of sp3-Enriched β-Fluoro Sulfonyl Chlorides

Rustam Gurbanov
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
,
Andriy Sokolov
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
Sergey Golovach
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
,
Kostiantyn Melnykov
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  Taras Shevchenko National University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
› Author Affiliations
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.

Supporting Information



Publication History

Received: 29 October 2020

Accepted after revision: 13 November 2020

Publication Date:
15 December 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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