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

TETRAHEDRON

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Article

Korotaev, Vladislav Yu.¹  Barkov, Alexey Yu.¹  Moshkin, Vladimir S.¹  Matochkina, Evgeniya G.²  Kodess, Mikhail I.²  Sosnovskikh, Vyacheslav Ya.¹ 

[1] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia

[2] Russian Acad Sci, Inst Organ Synth, Ural Branch, Ekaterinburg 620041, Russia

关键词: 3-Nitro-2H-chromenes;    Nonstabilized azomethine ylides;    1,3-Dipolar cycloaddition;    1-Benzopyrano[3,4-c]pyrrolidines;   

DOI  :  10.1016/j.tet.2013.07.080

来源: Elsevier

【 摘 要 】

Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-alpha-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the Delta(3)-bond of the chromene system. (C) 2013 Elsevier Ltd. All rights reserved.

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