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

Authors

  • 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
  • Oleksandr O. Grygorenko  *

    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

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 (online)


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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.

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