Enantiopure N-ferrocenylmethylaziridin-2-ylmethanols from L-serine: Synthesis, crystal structure and applications

  • Wang M
  • Wang D
  • Zhu Y
 et al. 
  • 5


    Mendeley users who have this article in their library.
  • 36


    Citations of this article.


A convenient and practical 'one-pot procedure' for the synthesis of methyl N-ferrocenylmethylaziridine-2-carboxylates 2 from the N-ferrocenylmethyl-L- serine methyl ester in the presence of p-toluenesulfonyl chloride and triethylamine is described. N-Ferrocenylmethylaziridin-2-ylmethanol 1 is a new type of β-amino alcohol ligand and is prepared from the corresponding methyl N-ferrocenylmethylaziridine-2-carboxylates 2 through a Grignard reaction. The crystal structures of compounds 1 and 2 reveal that the N-ferrocenylmethyl group is positioned anti to the hydroxymethyl group or ester group, respectively. X-ray analysis indicates that in aziridine alcohols 1, an intramolecular hydrogen bond is present in the crystalline state. The chiral ligands 1 were used as catalyst to promote the asymmetric addition of diethylzinc to benzaldehyde affording 1-phenylpropanol in up to 92.7% enantiomeric excess with excellent yields. © 2004 Elsevier Ltd. All rights reserved.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free