Aldol-type carbon bond formation of ethereal oxonium ylideElectronic supplementary information (ESI) available: experimental details, 1H NMR spectra and 13C NMR spectral data of compounds 1b, 2b, 4–7. See http://www.rsc.org/suppdata/cc/b1/b102248m/

Abstract

The Rh(2)-catalyzed reaction of 2-(3-diazo-1,1-dimethyl-2-oxopropyl)-2-methyldioxolane (1b) with arylaldehyde in the presence of (Me)₃SiCl and Ti(i-PrO)₄ gave 2-aryl-(hydroxy)methyl-8,8-dimethyl-7-methylene-3,6-dioxocane-1-one (6) and 2-aryl(hydroxy)methyl-4-(2-chloroethoxy)-4,5,5-trimethyl-3-oxacyclopentanone (7); these are the first examples of C–C bond formation of ethereal oxonium ylide via enol silyl ether intermediates.