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Enantiomerically enriched cryptone by lipase catalysed kinetic resolution
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.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Responsible organisation
2006 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 2, 275-280 p.Article in journal (Refereed) Published
Abstract [en]

Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanone) were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl-3-(phenylsulfanyl)cyclo¬he¬xanol which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The enantiomeric alcohols so obtained were oxidised. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively.

Place, publisher, year, edition, pages
2006. Vol. 17, no 2, 275-280 p.
Keyword [en]
cryptone, resolution, lipase, CAL-B
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-3720DOI: 10.1016/j.tetasy.2005.12.012ISI: 000235579500018Scopus ID: 2-s2.0-32444442897Local ID: 3886OAI: oai:DiVA.org:miun-3720DiVA: diva2:28752
Note

Corrigendum to "Enantiomerically enriched cryptone by lipase catalysed kinetic resolution". [Tetrahedron: Asymmetry 17 (2006) 275] (DOI:10.1016/j.tetasy.2005.12.012)

Tetrahedron Asymmetry Volume 17, Issue 8, 18 April 2006, Page 1318

DOI: 10.1016/j.tetasy.2006.04.028

ScopusID: 2-s2.0-33646837669

Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-28Bibliographically approved

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Isaksson, DanSjödin, KristinaHögberg, Hans-Erik
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