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

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,...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 7; no. 3; pp. 729 - 736
Main Authors Kolasa, Teodozyj, Stewart, Andrew O., Brooks, Clint D.W.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.03.1996
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ASTHMA
DERIVATIVES
ZILEUTON
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Summary: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. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(96)00068-7