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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.
KTH, School of Biotechnology (BIO), Biochemistry.
KTH, School of Biotechnology (BIO), Biochemistry.ORCID iD: 0000-0002-9577-832X
Mittuniversitetet.
2005 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 16, 2607-2611 p.Article in journal (Refereed) Published
Abstract [en]

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.
Keyword [en]
kinetic resolution, halohydrins, epoxides
National Category
Other Basic Medicine
Identifiers
URN: urn:nbn:se:kth:diva-6644DOI: 10.1016/j.tetasy.2005.06.028ISI: 000234625700013OAI: oai:DiVA.org:kth-6644DiVA: diva2:11409
Note
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 2010102Available from: 2005-09-21 Created: 2005-09-21 Last updated: 2010-10-20Bibliographically approved
In thesis
1. Enzymes as catalysts in synthesis of enantiomerically pure building blocks: secondary alcohols bearing two vicinal stereocenters
Open this publication in new window or tab >>Enzymes as catalysts in synthesis of enantiomerically pure building blocks: secondary alcohols bearing two vicinal stereocenters
2005 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Enzymes as tools in organic synthesis have provided enormous advantages. This thesis deals with the applications of enzymes in the kinetic resolutions of racemic compounds. The stereochemistry of chiral compounds and the kinetics of α/β hydrolase lipases are presented. From a practical point of view, the handling of a large number of parameters that influences the kinetic resolutions, especially enantioselectivity (E-value) are systematically described. A variety of approaches employed for raising the yields to over 50% are additionally discussed.

Methods for the preparation of synthetically useful chiral building blocks were developed in this thesis. Thus, resolution of secondary alcohols bearing two vicinal stereocentres are studied. These building blocks can serve as starting materials for the synthesis of various enantiomerically pure compounds for agrochemistry, pharmaceuticals, chemical industry, and particularly for the total synthesis of pheromones.

Racemic 3-substitued 2-hydroxybutane derivatives were produced in fairly high diastereomeric purities by a variety of chemical approaches, such as epimerization, metal-catalysed asymmetric addition etc. Kinetic resolution of these racemates was achieved by enzyme-catalysed reactions. Two lipases, Candida antarctica lipase B and Pseudomonas cepacia lipase were found to be useful in acylations as well as hydrolyses. In the biotransformations studied, the presence and nature of the second vicinal stereocentre in the chiral secondary alcohols investigated seemed to be important, e.g. in terms of the efficiencies of sequential kinetic resolutions, and altering the selectivities as well.

Place, publisher, year, edition, pages
Stockholm: KTH, 2005. vi, 65 p.
Series
Trita-IOK, ISSN 1100-7974 ; 2005:96
Keyword
enzyme, kinetic resolution, enantioselectivity, lipase, diastereoselectivity, epimerisation, metal-catalysed transformation, intramolecular alkylation.
National Category
Other Basic Medicine
Identifiers
urn:nbn:se:kth:diva-424 (URN)91-7178-129-3 (ISBN)
Public defence
2005-09-30, Sal K2, Teknikringen 28, Stockholm, 10:00
Opponent
Supervisors
Note
QC 20101020Available from: 2005-09-21 Created: 2005-09-21 Last updated: 2010-10-20Bibliographically approved

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Berglund, Per

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