An Expedient Approach to (2R,3S)-3-Azido-1,2-epoxy-4-phenylbutane: A key intermediate for HIV protease Inhibitors

Article abstract of DOI:10.1016/0957-4166(94)80039-1

A facile synthesis of the title product (1) starting from cis-butene-1,4-diol (2) has been described.The isomerised 3-butene-1,2-diol derivative 3 on Sharpless kinetic resolution with (+)-DIPT as a chiral auxiliary provided the enantiomerically pure epoxyalcohol (4).Successive opening of the epoxide (5) with PhMgBr, replacement of OH group with azide and derivatisation of the oxirane ring provided the requisite product 1.