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New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions
Journal article   Peer reviewed

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

Ozdemir Dogan, Hasan Koyuncu, Philip Garner, Adnan Bulut, Wiley J Youngs and Matthew Panzner
Organic letters, Vol.8(21), pp.4687-4690
10/12/2006
Handle:
https://hdl.handle.net/2376/106676
PMID: 17020278

Abstract

Glycine - analogs & derivatives Combinatorial Chemistry Techniques Glycine - chemistry Pyrrolidines - chemical synthesis Ligands Molecular Structure Catalysis Aziridines - chemistry Zinc - chemistry Pyrrolidines - chemistry
[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.

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