Tetrahedron letters

Conversion of isoxazolines to β-hydroxy esters. Synthesis of 2-deoxy-D-ribose

P Caldirola, M Ciancaglione, M De Amici…

Index: Caldilora, P.; Ciancaglione, M.; De Amici, M.; De Micheli, C. Tetrahedron Letters, 1986 , vol. 27, # 38 p. 4647 - 4650

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Citation Number: 29

Abstract

Typical procedure: To a suspension of dibromoformaldoxime (2mmol) and NaHCO 3 (15mmol) in ethyl acetate(15ml),an excess of dipolarophile(10mmol) is added. The slurry is stirred overnight then poured into water and extracted with ether.The residue of the organic phase is column chromatographed, the cycloadducts separated from furoxan and excess dipolarophile.In Entry 1 a two fold excess of 1,3-dipole was used.