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

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Abstract

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.

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Wang, M. C., Wang, D. K., Zhu, Y., Liu, L. T., & Guo, Y. F. (2004). Enantiopure N-ferrocenylmethylaziridin-2-ylmethanols from L-serine: Synthesis, crystal structure and applications. Tetrahedron Asymmetry, 15(8), 1289–1294. https://doi.org/10.1016/j.tetasy.2004.02.013

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