Synthesis of α‑C‑Stereochemically Pure Secondary Sulfonamides

A convenient “green” stereoretentive approach to sp 3 -enriched secondary sulfonamides bearing an asymmetric center at the α position to the sulfur atom is described. The method relies on the electrophilic amination of the corresponding stereochemically pure sulfinates with N-alkylhydroxylamine sulf...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-05, Vol.87 (9), p.6237-6246
Main Authors: Andriashvili, Vladyslav A, Zhersh, Serhii, Tolmachev, Andrey A, Grygorenko, Oleksandr O
Format: Article
Language:English
Subjects:
Amination
Stereoisomerism
Sulfonamides
Sulfonic Acids
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Summary:A convenient “green” stereoretentive approach to sp 3 -enriched secondary sulfonamides bearing an asymmetric center at the α position to the sulfur atom is described. The method relies on the electrophilic amination of the corresponding stereochemically pure sulfinates with N-alkylhydroxylamine sulfonic acids (in turn easily prepared from N-alkylhydroxylamine and HSO3Cl). It is shown that the efficiency of the approach is governed mainly by steric factors; its tolerance to several functional groups (e.g., ether, phthalimide, or N-Boc carbamate) is also demonstrated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00480