Asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea, a key intermediate for 5-lipoxygenase inhibitors

Article abstract of DOI:10.1016/0957-4166(96)00068-7

An efficient asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea from crotyl alcohol is described. The process involves asymmetric Sharpless epoxidation to establish the stereochemistry, formation of (S)-3-butynol and hydroxyl substitution with inversion by the masked N-hydroxyurea reagent N,O-bis(phenoxycarbonyl)hydroxylamine in a Mitsunobu reaction.