Synthesis 2019; 51(04): 848-858
DOI: 10.1055/s-0037-1611277
paper
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Cyclic sp3-Enriched cis-β-Alkoxysulfonyl Chlorides

Andriy Sokolov
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  National Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
Sergey Golovach
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
,
Ihor Kozlinsky
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
c  National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine   Email: gregor@univ.kiev.ua
,
Krystyna Dolia
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
c  National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine   Email: gregor@univ.kiev.ua
,
Andrey A. Tolmachev
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  National Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
Yuliya Kuchkovska
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  National Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
,
a  Enamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine   URL: www.enamine.net
b  National Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine
› Author Affiliations
This work was funded by Enamine Ltd.
Further Information

Publication History

Received: 07 September 2018

Accepted after revision: 01 October 2018

Publication Date:
22 October 2018 (eFirst)

Abstract

A three-step synthesis of β-alkoxy-substituted alicyclic sulfonyl chlorides from cyclic alkenes and alcohols is reported. The scope of the method was studied for a range of the substrates with various steric and electronic properties. The title compounds were obtained on a hundred-gram scale in up to 52% overall yield scale as single cis-diastereomers.

Supporting Information

 
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