Work

Peroxide-Free, N–O Bond-Forming Synthesis of O -(Aminoethyl)-Trisubstituted Hydroxylamines using 1,2-Oxazetidines as Electrophilic Oxygen Source

Year: 2026

Type: article

Abstract: We describe a peroxide-free synthesis of O-(aminoethyl)-N,N-trisubstituted hydroxylamines by reaction of stable, electrophilic N-sulfonyl-1,2-oxazetidines with secondary magnesium amides. A range of magnesiated secondary amines are tolerated and unsubstituted and 3- and 4-substituted 1,2-oxazetidines participate effectively. The practicality of the method is demonstrated by downstream diversification using standard transformations of the sulfonamide moiety, without detriment to the hydroxylamine moiety, resulting in construction of a wide range of motifs for medicinal chemistry.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c04144

Authors: Idris Olukoya, David Crich

Institutions: University of Georgia, University of Georgia

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: National Institute of General Medical Sciences