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

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 9...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2006-10, Vol.8 (21), p.4687-4690
Main Authors: Dogan, Özdemir, Koyuncu, Hasan, Garner, Philip, Bulut, Adnan, Youngs, Wiley J, Panzner, Matthew
Format: Article
Language:English
Subjects:
Aziridines - chemistry
Catalysis
Combinatorial Chemistry Techniques
Glycine - analogs & derivatives
Glycine - chemistry
Ligands
Molecular Structure
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
Zinc - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061521f