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The Rh(II)-catalyzed reaction of ethyl 2-diazo-3-(1-(ethoxycarbonyl)cyclopropyl)-3-oxo- propanecarboxylate with various dipolarophiles afforded dipolar cycloadducts in good yield. The reaction involves the formation of a rhodium carbenoid and subsequent transannular cyclization of the electrophilic carbon onto the remote ester carbonyl group to generate a five-membered cyclic carbonyl ylide which undergoes a subsequent dipolar cycloaddition reaction. In the absence of a trapping agent, a head to tail coupling of the 1,3-dipole intermediate occurs to give a dimer. Heating a benzene solution of the di mer at 80 oC in the presence of various dipolarophiles gave the same cycloadducts as was obtained from the Rh(II)-catalyzed reaction.

Generation of carbonyl ylide dipoles from the Rh(II) -catalyzed cyclization of α-diazo-β-keto-1,5-diesters