Russian Journal of Organic Chemistry

, Volume 44, Issue 3, pp 378–387

1,3-dipolar cycloaddition of schriff bases and electron-deficient alkenes, catalyzed by α-Amino acids

Authors

    • Faculty of ChemistryMoscow State University
  • A. A. Zagulyaeva
    • Faculty of ChemistryMoscow State University
Article

DOI: 10.1134/S1070428008030123

Cite this article as:
Kudryavtsev, K.V. & Zagulyaeva, A.A. Russ J Org Chem (2008) 44: 378. doi:10.1134/S1070428008030123

Abstract

L-α-Amino acids catalyze 1,3-dipolar cycloaddition of methyl α-benzylideneamino acids to electron-deficient olefins in different solvents at room temperature. L-α-Amino acids ensure stereoselective formation of the corresponding syn,syn-azomethine ylides. The subsequent reaction with an active dipolarophile is stereospecific; it occurs as endo-cycloaddition with low asymmetric induction (up to ee 12%.). 3,4-Substituted 5-arylprolines were obtained in preparative yields using L-pyroglutamic acid or L-proline as catalyst.

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© Pleiades Publishing, Ltd. 2008