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

Author:

Grygorenko Oleksandr12ORCID,Sokolov Andriy12,Golovach Sergey1,Kozlinsky Ihor13,Dolia Krystyna13,Tolmachev Andrey12,Kuchkovska Yuliya12

Affiliation:

1. Enamine Ltd.

2. National Taras Shevchenko University of Kyiv

3. National Technical University of Ukraine ‘Igor Sikorsky Kyiv Polytechnic Institute’

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.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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