Enantioselective Route to Ketones and Lactones from Exocyclic Allylic Alcohols via Metal and Enzyme Catalysis
2012 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 14, no 19, 5094-5097 p.Article in journal (Refereed) Published
A general and efficient route for the synthesis of enantiomerically pure a-substituted ketones and the corresponding lactones has been developed. Ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) with a subsequent Cu-catalyzed alpha-allylic substitution are the key steps of the route. The a-substituted ketones were obtained in high yields and with excellent enantiomeric excess. The methodology was applied to the synthesis of a naturally occurring caprolactone, (R)-10-methyl-6-undecanolide, via a subsequent Baeyer-Villiger oxidation.
Place, publisher, year, edition, pages
2012. Vol. 14, no 19, 5094-5097 p.
IdentifiersURN: urn:nbn:se:su:diva-82136DOI: 10.1021/ol302358jISI: 000309438400030OAI: oai:DiVA.org:su-82136DiVA: diva2:566666
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation