5,5-Dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups.
J Org Chem
; 67(14): 4833-8, 2002 Jul 12.
Article
en En
| MEDLINE
| ID: mdl-12098295
ABSTRACT
5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2002
Tipo del documento:
Article
País de afiliación:
Estados Unidos