Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

F. Faigl, Ervin Kovács, Gábor Turczel, Áron Szöllsy, Alessandro Mordini, László Balázs, Tamás Holczbauer, M. Czugler

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A novel, superbase induced diastereoselective transformation of benzylamino groups containing oxiranes has provided a series of trans-1,2,3-trisubstituted azetidines in good yields. The reaction of the corresponding optically active cis-2,3-disubstituted oxirane yielded the azetidine derivative as a single enantiomer. The structures of the new azetidines were confirmed by NMR spectroscopic methods and, in one case, by single crystal diffraction measurements.

Original languageEnglish
Pages (from-to)1607-1614
Number of pages8
JournalTetrahedron Asymmetry
Volume23
Issue number22-23
DOIs
Publication statusPublished - Dec 15 2012

Fingerprint

Azetidines
Enantiomers
enantiomers
Diffraction
Nuclear magnetic resonance
Single crystals
Derivatives
Ethylene Oxide
nuclear magnetic resonance
Epoxy Compounds
single crystals
synthesis
diffraction

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines. / Faigl, F.; Kovács, Ervin; Turczel, Gábor; Szöllsy, Áron; Mordini, Alessandro; Balázs, László; Holczbauer, Tamás; Czugler, M.

In: Tetrahedron Asymmetry, Vol. 23, No. 22-23, 15.12.2012, p. 1607-1614.

Research output: Contribution to journalArticle

Faigl, F, Kovács, E, Turczel, G, Szöllsy, Á, Mordini, A, Balázs, L, Holczbauer, T & Czugler, M 2012, 'Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines', Tetrahedron Asymmetry, vol. 23, no. 22-23, pp. 1607-1614. https://doi.org/10.1016/j.tetasy.2012.10.014
Faigl F, Kovács E, Turczel G, Szöllsy Á, Mordini A, Balázs L et al. Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines. Tetrahedron Asymmetry. 2012 Dec 15;23(22-23):1607-1614. https://doi.org/10.1016/j.tetasy.2012.10.014
Faigl, F. ; Kovács, Ervin ; Turczel, Gábor ; Szöllsy, Áron ; Mordini, Alessandro ; Balázs, László ; Holczbauer, Tamás ; Czugler, M. / Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines. In: Tetrahedron Asymmetry. 2012 ; Vol. 23, No. 22-23. pp. 1607-1614.
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