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Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres : the resolution of (± ) -4,4 -dimethyl -3 -phenyl -1 -pentanol
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2007 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 18, no 14, 1712-1720 p.Article in journal (Refereed) Published
Abstract [en]

Enantioselective acylation of some (±)-3-alkyl-3-phenyl-l-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the γ-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme® L-6/chloroform/vinyl propionate/38 °C and Chirazyme® L-7/di-iso-propyl ether/vinyl propionate/0 °C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (>98%) and in 25% and 22% yield, respectively.

Place, publisher, year, edition, pages
2007. Vol. 18, no 14, 1712-1720 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-7296DOI: 10.1016/j.tetasy.2007.07.002ISI: 000249710700012Scopus ID: 2-s2.0-34547932874OAI: oai:DiVA.org:miun-7296DiVA: diva2:127186
Available from: 2008-12-02 Created: 2008-12-02 Last updated: 2016-09-29Bibliographically approved

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