Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins

TETRAHEDRON

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Article

Moshkin, Vladimir S.¹  Sosnovskikh, Vyacheslav Ya.¹  Roeschenthaler, Gerd-Volker² 

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

[2] Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany

关键词: 3-Substituted coumarins;    Nonstabilized azomethine ylide;    [3+2] cycloaddition;    1-Benzopyrano[3,4-c]pyrrolidines;    Regioselectivity;    Stereoselectivity;   

DOI  :  10.1016/j.tet.2013.05.018

来源: Elsevier

【 摘 要 】

A three-component reaction of 3-substituted coumarins with N-alkyl-alpha-amino acids and aldehydes gave 1-benzopyrano[3,4-c]pyrrolidines as a result of a 1,3-dipolar cycloaddition of an intermediate non-stabilized azomethine ylide at the double bond of the coumarin system in moderate to good yields. In most cases, high regio- and stereo-selectivity of the [3+2] cycloaddition was observed. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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