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 language | English |
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Pages (from-to) | 582-600 |
Number of pages | 19 |
Journal | Tetrahedron: Asymmetry |
Volume | 21 |
Issue number | 5 |
DOIs | |
Publication status | Published - 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