title: Dynamic kinetic resolution of homoallylic alcohols: application to the synthesis of enantiomerically pure 5,6-dihydropyran-2-ones and δ-lactones.
abstract: Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B 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 carboncarbon double bond afforded the corresponding δ-lactones without loss of chiral information.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm (Sweden).
authors.forename: Madeleine C
authors.initials: MC
authors.lastname: Warner
authors.forename: Grigory A
authors.initials: GA
authors.lastname: Shevchenko
authors.forename: Suzan
authors.initials: S
authors.lastname: Jouda
authors.forename: Krisztián
authors.initials: K
authors.lastname: Bogár
authors.forename: Jan-E
authors.initials: JE
authors.lastname: Bäckvall
mesh_terms: D000085:Acetates / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006868:Hydrolysis; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000438:Alcohols; D007783:Lactones; D011753:Pyrones; D012428:Ruthenium
keywords: dynamic kinetic resolution; homoallylic alcohols; lactones; racemization; ruthenium catalysis