Preparation of the four stereoisomers of 3-bromo-2-butanol or their acetates via lipase-catalysed resolutions of the racemates derived from dl- or meso-2,3-butanediol.
2005 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 16, 2607-2611 p.Article in journal (Refereed) Published
The four stereoisomeric 3-bromo-2-butanols and/or their acetates were prepared via lipase-catalysed kinetic resolution by hydrolyses of the acetates of the (+/-)-syn- and (+/-)-anti-3-bromo-2-butanols, or via esterifications of the alc hols. The diastereomeric bromoacetates were obtained by syntheses from the dl- and meso-2,3-butanediols, respectively. On a preparative scale, the four stereoisomers, either as the free alcohols or as their acetates, were obtained in > 95% ee, and in 35-40% yield (based on the starting racemates).
Place, publisher, year, edition, pages
2005. Vol. 16, 2607-2611 p.
kinetic resolution, halohydrins, epoxides
Other Basic Medicine
IdentifiersURN: urn:nbn:se:kth:diva-6644DOI: 10.1016/j.tetasy.2005.06.028ISI: 000234625700013OAI: oai:DiVA.org:kth-6644DiVA: diva2:11409
Tidigare titel: Lipase-catalysed kinetic resolution furnishes the four stereoisomers of 3-bromo-2-butanol or its acetate from d,l- and meso-2,3-butanediol.
QC 20101022005-09-212005-09-212010-10-20Bibliographically approved