title: Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful reactants for Lewis acid catalyzed [4 + 3] cyclizations.
abstract: [reaction: see text]. Retrocycloadditions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereoselectivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.
authors.affiliation: Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: R A
authors.initials: RA
authors.lastname: Aungst
authors.forename: R L
authors.initials: RL
authors.lastname: Funk
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004147:Dioxins / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004147:Dioxins; D012833:Siloxanes