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1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines

V. S. Moshkin^a, V. Ya. Sosnovskikh^a, P. A. Slepukhin^b, G.-V. Roeschenthaler<sup>c

a</sup> Department of Chemistry, Ural Federal University, Ekaterinburg, Russian Federation
^b I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^c School of Engineering and Science, Jacobs University of Bremen, Bremen, Germany

Abstract: Reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes proceeds regio- and stereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines as a result of 1,3-dipolar cycloaddition of the intermediate azomethine ylides at the Δ³-bond of the coumarins.

Language: English

DOI: 10.1016/j.mencom.2012.01.011

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