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

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 scal...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2019-02, Vol.51 (4), p.848-858
Main Authors: Sokolov, Andriy, Golovach, Sergey, Kozlinsky, Ihor, Dolia, Krystyna, Tolmachev, Andrey A., Kuchkovska, Yuliya, Grygorenko, Oleksandr O.
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1611277