Tetrahedron: Asymmetry

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

T Kolasa, AO Stewart, CDW Brooks

Index: Kolasa, Teodozyj; Stewart, Andrew O.; Brooks, Clint D. W. Tetrahedron Asymmetry, 1996 , vol. 7, # 3 p. 729 - 736

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Citation Number: 30

Abstract

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.

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