Experimental and theoretical study of the [3+2] cycloaddition of
carbonylylides with alkynes
GheniaBentabed-Ababsa,*Samira Hamza-Reguig,aAïchaDerdour,Luis R. Domingo,*José A. Sáez,Thierry Roisnel,Vincent Dorcet,EkhlassNassarand Florence Mongin*, Org. Biomol. Chem., 2012,10, 8434
Abstract
The [3+2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes(phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to givesubstituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the10 reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between
the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoreticallyinvestigated using DFT methods in order to explain the reactivity and regioselectivity observed.
