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

Dogan O., KOYUNCU H., GARNER P., BULUT A., Youngs W. J., PANZNER M.

ORGANIC LETTERS, vol.8, no.21, pp.4687-4690, 2006 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 8 Issue: 21
  • Publication Date: 2006
  • Doi Number: 10.1021/ol061521f
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4687-4690
  • Middle East Technical University Affiliated: Yes

Abstract

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.