title: Polysubstituted oxygen heterocycles by a Reformatsky-type reaction/reductive cyclization approach from enantiopure beta-ketosulfoxides.
abstract: The stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by reductive cyclization (Et3SiH/TMSOTf) from the corresponding enantiopure hydroxy ketones protected as a dioxolane. These derivatives are easily accessible from a Reformatsky-type reaction between alpha-bromo-alpha'-sulfinyl ketones and protected alpha- or beta-ketoaldehydes, followed by diastereoselective reduction of the resulting beta-ketosulfoxide.
authors.affiliation: Laboratoire de Stéréochimie associé au CNRS, UMR 7509, Université Louis Pasteur, ECPM 25 rue Becquerel, 67087 Strasbourg Cedex 2, France. fcolober@chimie.u-strasbg.fr
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
authors.forename: Sabine
authors.initials: S
authors.lastname: Choppin
authors.forename: Leticia
authors.initials: L
authors.lastname: Ferreiro-Mederos
authors.forename: Michel
authors.initials: M
authors.lastname: Obringer
authors.forename: Sandra Luengo
authors.initials: SL
authors.lastname: Arratta
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño