N-Methylhydroxylamine-O-sulfonic acid

CAS 3400-11-1, Cat. No EN300-26864957

Reagent for amination

N-Methylhydroxylamine-O-sulfonic acid is an electrophilic amination reagent used for the stereoretentive synthesis of secondary sulfonamides¹. It reacts with optically active sulfinates in water to deliver chiral sulfonamides with high diastereo- and enantioselectivity. The method proceeds under mild, environmentally friendly conditions with excellent yields and broad tolerance to various functional groups. It enables access to over 50 stereochemically pure sulfonamides and is scalable for practical synthesis. The reagent is especially effective for substrates with primary N-alkyl groups, offering a straight and sustainable route to valuable chiral building blocks.

Synonyms: [(methylamino)oxy]sulfonic acid; hydroxylamine-O-sulfonic acid, N-methyl- ;methylazanyl hydrogen sulfate; N-methylhydroxylamine O-hydrosulfate; sulfuric acid, mono(methylazanyl) ester

Selected publication

1. Synthesis of α-C-Stereochemically Pure Secondary Sulfonamides.Andriashvili, V. A.; Zhersh, S.; Tolmachev, A. A.; Grygorenko, O. O. J Org Chem 2022, 87 (9), 6237–6246. DOI: 10.1021/acs.joc.2c00480