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Rhodium-catalyzed synthesis of 2,3 – Disubstituted N-methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins

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Abstract For the first time, we report the synthesis of 2-substituted N -alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α -diazo carbonyl… Click to show full abstract

Abstract For the first time, we report the synthesis of 2-substituted N -alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α -diazo carbonyl compounds with vinyl equivalents in a one-pot process. We have demonstrated ethyl vinyl ether as well as vinyl acetate as vinyl equivalents and both were found to give excellent yields. We have also demonstrated the synthesis of N -alkoxy dihydropyrrole derivatives by carrying out the reaction at low temperature.

Keywords: cycloaddition; rhodium catalyzed; disubstituted methoxy; synthesis disubstituted; catalyzed synthesis; synthesis

Journal Title: Tetrahedron
Year Published: 2017

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