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. [10.1016/S0040-4020(01)82075-5]
METAL-HYDRIDE REDUCTION OF ISOXAZOLINE-3-CARBOXYLATE ESTERS
M. De AmiciSecondo
;C. De Micheli;
1986
Abstract
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.
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