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. © 1986.
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CITATION STYLE
Caldirola, P., De Amici, M., De Micheli, C., Wade, P. A., Price, D. T., & Bereznak, J. F. (1986). Metal-hydride reduction of isoxazoline-3-carboxylate esters. Tetrahedron, 42(19), 5267–5272. https://doi.org/10.1016/S0040-4020(01)82075-5
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