Chiral relay in NHC-mediated asymmetric beta-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines

Nicolas Duguet, Adele Donaldson, Stuart M. Leckie, Eddy A. Kallstrom, Craig D. Campbell, Peter Shapland, Thomas B. Brown, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)601-616
Number of pages16
JournalTetrahedron: Asymmetry
Volume21
Issue number5
DOIs
Publication statusPublished - 30 Mar 2010

Keywords

  • N-HETEROCYCLIC CARBENE
  • ALPHA-AMINO-ACIDS
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • CATALYZED CONJUGATE ADDITION
  • C-CARBOXYL TRANSFER
  • LEWIS-ACID
  • DISUBSTITUTED KETENES
  • 4+2 CYCLOADDITION
  • CONVEY ASYMMETRY
  • ACHIRAL LIGANDS

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