title: First enantioselective synthesis of vinyl oxiranes from aldehydes and ylides generated from allyl halides and chiral sulfides.
abstract: Asymmetric allylidenation of aldehydes with sulfur ylides is possible with proper substitution of the initial sulfide, to avoid the [2,3] sigmatropic rearrangement of the unsaturated ylides. One-pot reaction of (2R,5R)-dimethylthiolane with allyl halides, aldehydes, and sodium hydroxide in tert-butyl alcohol affords vinyl oxiranes in good yields. Enantiomeric excesses up to 90% and trans selectivities have been achieved with methallyl-type halides.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université de Caen, 6 Boulevard du Maréchal Juin, F-14050 Caen, France.
authors.forename: Jacques
authors.initials: J
authors.lastname: Zanardi
authors.forename: David
authors.initials: D
authors.lastname: Lamazure
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Minière
authors.forename: Vincent
authors.initials: V
authors.lastname: Reboul
authors.forename: Patrick
authors.initials: P
authors.lastname: Metzner