New Zinc(II)-Based Catalyst for Asymmetric Azomethine Ylide Cycloaddition Reactions

Özdemir Dogan,*† Hasan Koyuncu,† Philip Garner,*‡ Adnan Bulut,§ Wiley J. Youngs, and Matthew Panzner;
Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey, Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106-7078, Department of Chemistry, Kirikkale University, 71450 Kirikkale, Turkey, and Department of Chemistry, University of Akron, Akron, Ohio 44325
Org. Lett., 2006, 8 (21), pp 4687–4690
DOI: 10.1021/ol061521f
Publication Date (Web): September 9, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Middle East Technical University.

,
‡

 Case Western Reserve University.

,
§

 Kirikkale University.

,

 University of Akron.

, dogano@metu.edu.tr, ; , ppg@case.edu

Abstract

Abstract Image

A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.

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History

  • Published In Issue October 12, 2006
  • Received June 21, 2006

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