A novel transformation of primary amines to N-monoalkylhydroxylamines

Authors
Tokuyama, H Kuboyama, T Amano, A Yamashita, T Fukuyama, T
Citation
H. Tokuyama et al., A novel transformation of primary amines to N-monoalkylhydroxylamines, SYNTHESIS-S, (9), 2000, pp. 1299-1304
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
9
Year of publication
2000
Pages
1299 - 1304
Database
ISI
SICI code
0039-7881(200008):9<1299:ANTOPA>2.0.ZU;2-J
Abstract
A novel transformation of primary amines to the corresponding N-monoalkylhy droxylamines is described. The three-step protocol involves selective mono- cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamin e hydrochloride. The method is applicable for a wide range of primary amine s, including alkyl, benzyl, and chiral.