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Beilstein J. Org. Chem. 2013, 9, 2422–2433, doi:10.3762/bjoc.9.280
Graphical Abstract
Figure 1: Chiral gold(I) complexes employed in 1,3-DC involving azomethine ylides.
Scheme 1: 1,3-DC of azlactone 5a and NPM.
Scheme 2: General 1,3-DC between azlactones 5 with maleimides.
Scheme 3: Formation of the amide 8aa.
Figure 2: Positive non-linear effects (NLE) observed in 1,3-DC of azlactone 7aa and NPM.
Figure 3: Main geometrical features and relative Gibbs free energies (in kcal mol−1 at 298 K) of complexes [(S...
Figure 4: Main geometrical features and relative Gibbs free energies (in kcal mol−1) of the less energetic tr...
Scheme 4: Reaction Gibbs free energy associated with the 1,3-DC of 5aa and NPM catalyzed by (Sa)-Binap gold d...
Scheme 5: ΔG calculation for the recovery of the catalytic active species.
Scheme 6: 1,3-DC of azlactone 10 and tert-butyl acrylate.
Figure 5: (A) Schematic representation of the model gold(I) ylides. (B) HOMO of the ylides and expansion orbi...
Figure 6: Main geometrical features and relative Gibbs free energies (in kcal mol−1 at 298 K) of complexes [{(...
Figure 7: Main geometrical features and relative Gibbs free energies (in kcal mol−1) of the less energetic tr...
Scheme 7: Reduction of heterocycle 7aa under different conditions.
Scheme 8: Double 1,3-DC to give polycycle 15.
Scheme 9: Reaction between 7aa and nitrostyrene.