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Oxidative preparation of optically active n-hydroxy-α-amino acid amides

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
46
Issue
5
Identifiers
DOI: 10.1016/s0040-4020(01)81979-7

Abstract

Abstract Two routes are presented for the conversion of optically active α-amino acid amides into the title compounds. One route(route A) features the formation of the Schiff's base 6 which is subsequently oxidized to the corresponding oxaziridines 7. Route B is characterized by the formation of an imidazolin 11 which is hydroxylated to compound 12. Alcoholysis of 7 and 12 in the presence of hydroxylamine hydrochloride yields the title compounds in overall yields ringing from 65 to 85%(route A) and from 14 to 21%(route B).

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