New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions

Ozdemir Dogan; Hasan Koyuncu; Philip Garner; Adnan Bulut; Wiley J Youngs; Matthew Panzner

doi:10.1021/ol061521f

New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions

Org Lett. 2006 Oct 12;8(21):4687-90. doi: 10.1021/ol061521f.

Authors

Ozdemir Dogan¹, Hasan Koyuncu, Philip Garner, Adnan Bulut, Wiley J Youngs, Matthew Panzner

Affiliation

¹ Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. dogano@metu.edu.tr

PMID: 17020278
DOI: 10.1021/ol061521f

Abstract

[reaction: see text] 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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aziridines / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Glycine / analogs & derivatives*
Glycine / chemistry
Ligands
Molecular Structure
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Zinc / chemistry*

Substances

Aziridines
Ligands
Pyrrolidines
glycine methyl ester
Zinc
Glycine