title: A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and alpha, beta-unsaturated delta-valero lactones.
abstract: The synthesis of arylated dihydropyrans and unsaturated lactones starting from enantiomerically pure alpha-hydroxy ketones (prepared by an enzyme-catalyzed benzoin condensation) is described. The key steps are a highly diastereoselective addition of vinyl metal compounds under chelate control and a ruthenium-catalyzed ring-closing olefin metathesis reaction. Elucidation of the relative configuration of the final products was achieved by NOE experiments.
authors.affiliation: FB Chemie der Universität Dortmund, Organische Chemie, D-44221 Dortmund, Germany.
authors.forename: Holger
authors.initials: H
authors.lastname: Wildemann
authors.forename: Pascal
authors.initials: P
authors.lastname: Dünkelmann
authors.forename: Michael
authors.initials: M
authors.lastname: Müller
authors.forename: Bernd
authors.initials: B
authors.lastname: Schmidt