Enantiomerically enriched cryptone by lipase catalysed kinetic resolution
2006 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 2, 275-280 p.Article in journal (Refereed) Published
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)cyclohexanol, which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The alcohol enantiomers obtained were oxidised. The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. 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.
IdentifiersURN: urn:nbn:se:kth:diva-8992DOI: 10.1016/j.tetasy.2005.12.012ISI: 000235579500018OAI: oai:DiVA.org:kth-8992DiVA: diva2:14517
Tidigare titel:Enantiomerically enriched cryptone obtained by lipase catalysed resolution.2006-01-162006-01-162010-12-08Bibliographically approved