title: Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: asymmetric synthesis of polypropionate fragments.
abstract: At low temperature, 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or protic acid generating zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma-unsaturated silyl sulfinates can be desilylated by 1:1 Pd(OAc)(2)/PPh(3) catalyst, liberating the corresponding beta,gamma-unsaturated sulfinic acids that undergo smooth and highly stereoselective retro-ene eliminations of sulfur dioxide. The method has been applied to generate enantiomerically pure polypropionate fragments.
authors.affiliation: Laboratory of Glycochemistry and Asymmetric Synthesis, Swiss Federal Institute of Technology, EPFL-BCH, CH-1015 Lausanne-Dorigny, Switzerland.
authors.forename: Xiaogen
authors.initials: X
authors.lastname: Huang
authors.forename: Cotinica
authors.initials: C
authors.lastname: Craita
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel