A novel oxidative cyclisation onto vinyl silanes.
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.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Winship
Paul C M
PC
Pilgrim
Ben S
BS
Walter
Daryl S
DS
Callens
Cedric K A
CK
D003500:Cyclization; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*
D012821:Silanes