Tetrahedron

Metal-hydride reduction of isoxazoline-3-carboxylate esters

P Caldirola, M De Amici, C De Micheli, PA Wade…

Index: Caldirola, Patrizia; De Amici, Marco; De Micheli, Carlo; Wade, Peter A.; Price, David T.; Bereznak, James F. Tetrahedron, 1986 , vol. 42, # 19 p. 5267 - 5272

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Citation Number: 16

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 ...