Russian Journal of Organic Chemistry

, Volume 44, Issue 3, pp 378–387 | Cite as

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

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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.

Keywords

Schiff Base Optical Purity Dimethyl Fumarate Pyrrolidine Ring Azomethine Ylide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Copyright information

© Pleiades Publishing, Ltd. 2008

Authors and Affiliations

  1. 1.Faculty of ChemistryMoscow State UniversityMoscowRussia

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