Article citationsMore>>

N. Duguet, A. Donaldson, S. M. Leckie, J. Douglas, P. Shapland, T. B. Brown, G. Churchill, A. M. Z. Slawin and A. D. Smith, “Chiral Relay in NHC-Mediated Asy- mmetric ?-Lactam Synthesis I; Substituent Effects in NHCs Derived from (1R,2R)-Cyclohexane-1,2-diamine,” Tetrahedron: Asymmetry, Vol. 21, No. 5, 2010, pp. 582- 600. doi:10.1016/j.tetasy.2010.03.001

has been cited by the following article:

• TITLE: Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid

  AUTHORS: Marta Feroci

  KEYWORDS: Electrosynthesis, NHC, Staudinger Synthesis, ?-Lactams, Organocatalyst, Ionic Liquid

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.1 No.4, December 27, 2011

  ABSTRACT: Electrogenerated N-heterocyclic carbene (NHC), obtained by cathodic reduction of Bmim-BF4, behaves as organocatalyst and base in the Staudinger synthesis from an acyl chloride and a deactivated imine in ionic liquid to yield ?-lactams. The effect of many parameters (temperature, amount of electricity, substituents, presence of an external base) has been evaluated and a tentative mechanism for the Staudinger synthesis in a very polar medium like the ionic liquid reported. The yields of isolated ?-lactams are good, starting from non-electrophilic imines, and predominantly trans lactams are obtained with a good diastereomeric ratio.