Predicting the equilibrium of enamine formation

Jaume Vilarassa and co-workers at Universitat de Barcelona in Spain have reported in Organic Letters on the tendency to form specific enamines in the presence of different carbonyl groups – for example aldehydes are more reactive in ketones generally except in the case where 1,3-dihydroxyacetone acetals are used as substrates to give rise to the enamine over alpha-branched aldehydes.

OL paper