title: One-pot catalytic asymmetric synthesis of pyranones.
abstract: Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%.
authors.affiliation: P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Kevin
authors.initials: K
authors.lastname: Cheng
authors.forename: Ann Rowley
authors.initials: AR
authors.lastname: Kelly
authors.forename: Rachel A
authors.initials: RA
authors.lastname: Kohn
authors.forename: Jessica F
authors.initials: JF
authors.lastname: Dweck
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000478:Alkylation; D002384:Catalysis; D005662:Furaldehyde / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D005663:Furans; D011753:Pyrones; D005662:Furaldehyde; D015032:Zinc