Chiral relay in NHC-mediated asymmetric beta-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine

Nicolas Duguet, Adele Donaldson, Stuart M. Leckie, James Douglas, Peter Shapland, Thomas B. Brown, Gwydion Churchill, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

The synthesis of a range of C-2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)582-600
Number of pages19
JournalTetrahedron: Asymmetry
Volume21
Issue number5
DOIs
Publication statusPublished - 30 Mar 2010

Keywords

  • N-HETEROCYCLIC CARBENE
  • DIELS-ALDER REACTIONS
  • INTRAMOLECULAR STETTER REACTION
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • CATALYZED RING EXPANSION
  • C-CARBOXYL TRANSFER
  • ALPHA-AMINO-ACIDS
  • ALPHA,BETA-UNSATURATED ALDEHYDES
  • KINETIC RESOLUTION
  • LEWIS-ACID

Fingerprint

Dive into the research topics of 'Chiral relay in NHC-mediated asymmetric beta-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine'. Together they form a unique fingerprint.

Cite this