title: Further studies on silatropic carbonyl ene cyclisations: beta-crotyl(diphenyl)silyloxy aldehyde substrates; synthesis of 2-deoxy-2-C-phenylhexoses.
abstract: Silatropic carbonyl ene cyclisations of beta-(allylsilyloxy)- and beta-(crotylsilyloxy)butyraldehydes are shown to proceed with high stereoselectivity but at a much reduced rate in comparison to the cyclisation of analogous alpha-substrates. In the second section, olefin cross-metathesis is explored as a route to substituted alpha-(allylsilyloxy)aldehydes and the method applied to the synthesis of diastereomeric 2-deoxy- and 2-deoxy-2-C-phenyl hexose derivatives from butanediacetal-protected D-glyceraldehyde.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. jeremy.robertson@chem.ox.ac.uk
authors.forename: Jeremy
authors.initials: J
authors.lastname: Robertson
authors.forename: Stuart P
authors.initials: SP
authors.lastname: Green
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Hall
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Tyrrell
authors.forename: William P
authors.initials: WP
authors.lastname: Unsworth
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D006601:Hexoses; D017646:Organosilicon Compounds; D012825:Silicon