Synthesis of 1H-Furo- and Pyrrolo[3,4-c]pyrrole Derivatives by Multicomponent Reactions

Significance

A three-component reaction for the synthesis of functionalized tetrahydro-1H-furo- and pyrrolo[3,4-c]pyrrole derivatives involving a key [3+2] cycloaddition in moderate to high yields is reported. The reaction proceeds under mild conditions for aliphatic and aromatic aldehydes via in situ dipolarophile formation followed by [2+3] dipolar cycloaddition. Endo selectivity was observed with both N-phenyl maleimide and maleic anhydride. The method was also applied using methyl acrylate as the dipolarophile in the presence of a catalytic amount of AgOAc to give products with good chemo-, regio-, and stereoselectivities.