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Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation: Tetrahedron: Asymmetry
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
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2005 (English)In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 16, no 7, 1355-1360 p.Article in journal (Refereed) Published
Abstract [en]

Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (alpha-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (beta-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E > 400) was obtained when Novozyme 435 was used as the catalyst at a water activity of a(w) similar to 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl-pentan-1,4-diol, were obtained in very high diastereomeric (> 99% de) and enantiomeric purities (> 99.8% and > 97.4% ee, respectively).

Place, publisher, year, edition, pages
2005. Vol. 16, no 7, 1355-1360 p.
Keyword [en]
Lipase, stereoselective, synthesis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-1637DOI: 10.1016/j.tetasy.2005.01.043ISI: 000228194800011Scopus ID: 2-s2.0-27644560973Local ID: 3999OAI: oai:DiVA.org:miun-1637DiVA: diva2:26669
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-29Bibliographically approved

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CiteExportLink to record
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Citation style
  • apa
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  • modern-language-association-8th-edition
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