An Investigation of the Enolization and Isomeric Products Distribution in the Water Promoted Aldol Reaction of Tropinone and Granatanone

Figure 7

The classical adiabatic ground state () potential energy curve along the reaction coordinates of the aldol addition of tropinone enol (a, b) and granatanone enol (c, d) to benzaldehyde proceeding to the exo,syn (a, c) and the exo,anti (b, d) isomers. The activation energies (), reaction energies (), and differences of energies () of the HB-N and HB-O forms of the isomeric products are shown in red. For the sake of comparison, the corresponding free energies differences () are given in blue. Note that the ordinates correspond to the energies () not free energies (), so the blue values cannot be figured out from the chart.

(a)

(b)

(c)

(d)