Dynamic Kinetic Resolution of Homoallylic Alcohols: Application to the Synthesis of Enantiomerically Pure 5,6-Dihydropyran-2-ones and delta-Lactones
2013 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 41, 13859-13864 p.Article in journal (Refereed) Published
Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipaseB and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transformed into homoallylic acrylates after hydrolysis of the ester function and subsequent DMAP-catalyzed esterification with acryloyl chloride. After ring-closing metathesis 5,6-dihydropyran-2-ones were obtained in good yields. Selective hydrogenation of the carboncarbon double bond afforded the corresponding -lactones without loss of chiral information.
Place, publisher, year, edition, pages
2013. Vol. 19, no 41, 13859-13864 p.
dynamic kinetic resolution, homoallylic alcohols, lactones, racemization, ruthenium catalysis
IdentifiersURN: urn:nbn:se:su:diva-95745DOI: 10.1002/chem.201301980ISI: 000325135800031OAI: oai:DiVA.org:su-95745DiVA: diva2:662291
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation