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

Andriy Sokolov; Sergey Golovach; Ihor Kozlinsky; Krystyna Dolia; Andrey A. Tolmachev; Yuliya Kuchkovska; Oleksandr O. Grygorenko

doi:10.1055/s-0037-1611277

Synthesis, Table of Contents

Synthesis 2019; 51(04): 848-858
DOI: 10.1055/s-0037-1611277

paper

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

Andriy Sokolov

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bNational Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Sergey Golovach

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

,

Ihor Kozlinsky

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^cNational Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine Email: gregor@univ.kiev.ua

,

Krystyna Dolia

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^cNational Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’, Prospect Peremogy 37, Kyiv 03056, Ukraine Email: gregor@univ.kiev.ua

,

Andrey A. Tolmachev

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bNational Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Yuliya Kuchkovska

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bNational Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

,

Oleksandr O. Grygorenko *

^aEnamine Ltd., Chervonotkatska Street 78, Kyiv 02094, Ukraine URL: www.enamine.net

^bNational Taras Shevchenko University of Kyiv, Volodymyrska Street 60, Kyiv 01601, Ukraine

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Abstract

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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.

Key words

organosulfur compounds - alicyclic compounds - heteroaliphatic compounds - sulfonyl chlorides - building blocks

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References

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