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J. Org. Chem. 2022, 87 (9), 6237-6246

DOI: 10.1021/acs.joc.2c00480

Andriashvili V.; Zhersh S.; Tolmachev A.; Grygorenko O.

A convenient “green” stereoretentive approach to sp3-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.

 

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