title: Stereocontrolled (Me3Si)3SiH-Mediated Radical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted THF.
abstract: 2,3,5-Trisubstituted tetrahydrofurans were prepared stereoselectively through a two-step process involving the addition of an acyl radical to a β-silyloxy acrylic ester followed by an acid-catalyzed desilylation-ketalization sequence and a final oxocarbenium reduction step. High levels of 1,2- and 1,3-stereocontrol were attained when (Me3Si)3SiH was used as a radical followed by a ionic hydrogen transfer agent.
authors.affiliation: University of Bordeaux , Institute of Molecular Sciences, UMR-CNRS 5255, 351 cours de la libération, 33405 Talence, France.
authors.forename: Simon
authors.initials: S
authors.lastname: Grélaud
authors.affiliation: University of Bordeaux , Institute of Molecular Sciences, UMR-CNRS 5255, 351 cours de la libération, 33405 Talence, France.
authors.forename: Valérie
authors.initials: V
authors.lastname: Desvergnes
authors.affiliation: University of Bordeaux , Institute of Molecular Sciences, UMR-CNRS 5255, 351 cours de la libération, 33405 Talence, France.
authors.forename: Yannick
authors.initials: Y
authors.lastname: Landais