MECHANISTIC INSIGHTS FROM AB-INITIO CALCULATIONS ON A NITROGEN ANALOG OF THE BORON MEDIATED ALDOL REACTION

Molecular orbital calculations were used to study a nitrogen analogue of the boron mediated aldol reaction. Experimental results show that high selectivity can be obtained in some cases, at the cost of low yields. The molecular orbital calculations are used to analyse the experimental results and to suggest modifications to the experimental procedure. The results suggest an explanation for a puzzling reversal of selectivity in the aldol reactions of methyl ketones.