title: A novel oxidative cyclisation onto vinyl silanes.
abstract: A novel osmium-catalysed oxidative cyclisation of 1,2-diols bearing a pendant vinyl silane affords THFs that contain silicon functionality at the ring junction. When the cyclisation occurs onto a vinyl benzyldimethylsilyl group, the resulting silyl group can act as a masked hydroxyl group and undergo a Fleming-Tamao type oxidation at a later stage to form the corresponding lactol. The scope of this reaction can also be extended beyond 1,2-diols and applied to the cyclisation of α-hydroxy-sulfonamides and α-hydroxy-amides.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Paul C M
authors.initials: PC
authors.lastname: Winship
authors.forename: Ben S
authors.initials: BS
authors.lastname: Pilgrim
authors.forename: Daryl S
authors.initials: DS
authors.lastname: Walter
authors.forename: Cedric K A
authors.initials: CK
authors.lastname: Callens
mesh_terms: D003500:Cyclization; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*
chemical_list: D012821:Silanes