Highly diastereoselective 1,3-dipolar cycloaddition of nonstabilized azomethine ylides to 3-nitro-2-trihalomethyl-2H-chromenes: synthesis of 1-benzopyrano[3,4-c]pyrrolidines |
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| Authors: | Vladislav Yu Korotaev Alexey Yu Barkov Vladimir S Moshkin Evgeniya G Matochkina Mikhail I Kodess Vyacheslav Ya Sosnovskikh |
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| Institution: | 1. Department of Chemistry, Ural Federal University, 620000 Ekaterinburg, Russian Federation;2. Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620041 Ekaterinburg, Russian Federation |
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| Abstract: | Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-α-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the Δ3-bond of the chromene system. |
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| Keywords: | 3-Nitro-2H-chromenes Nonstabilized azomethine ylides 1 3-Dipolar cycloaddition 1-Benzopyrano[3 4-c]pyrrolidines |
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