The reduction of a series of isoxazolino-3-carboxylate esters with sodium borohydride gave 3-(hydroxymethyl)isoxazolines in 34-98% yield. Reduction with DIBAH gave isoxazoline-3-carboxaldehydes in 63 and 85% yields for the two reactions studied. Isoxazoline-3-carboxaldehydes could also be prepared by Swern oxidation of the corresponding 3-(hydroxymethyl)isoxazolines. The hydroxyl group of 3-(hydroxymethyl)isoxazoline 11b was silylated and the endocyclic double bond was cleaved by ozonolysis to produce a monosilylated triol.
METAL-HYDRIDE REDUCTION OF ISOXAZOLINE-3-CARBOXYLATE ESTERS / P: Caldirola, M. De Amici, C. De Micheli, P. A. Wade, D. T. Price, J. F. Bereznak. - In: TETRAHEDRON. - ISSN 0040-4020. - 42:19(1986), pp. 5267-5272.
Titolo: | METAL-HYDRIDE REDUCTION OF ISOXAZOLINE-3-CARBOXYLATE ESTERS |
Autori: | DE AMICI, MARCO (Secondo) |
Settore Scientifico Disciplinare: | Settore CHIM/08 - Chimica Farmaceutica |
Data di pubblicazione: | 1986 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0040-4020(01)82075-5 |
Appare nelle tipologie: | 01 - Articolo su periodico |