Further studies on silatropic carbonyl ene cyclisations: beta-crotyl(diphenyl)silyloxy aldehyde substrates; synthesis of 2-deoxy-2-C-phenylhexoses.
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.
Robertson
Jeremy
J
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. jeremy.robertson@chem.ox.ac.uk
Green
Stuart P
SP
Hall
Michael J
MJ
Tyrrell
Andrew J
AJ
Unsworth
William P
WP
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*
D000447:Aldehydes; D000475:Alkenes; D006601:Hexoses; D017646:Organosilicon Compounds; D012825:Silicon