The results on the multicomponent reaction between cyclic β-keto esters, enals, and
simple primary aliphatic amines are reported. In thermal conditions in the presence
of 4 Å molecular sieves, two different families of heterocyclic products (aminobicyclo[3.3.1]nonanones
or cycloalka[b]piperidines) were obtained depending on the presence of a substituent in the α-position
of the aldehyde. Moreover, preliminary results on the possibility to obtain these
two bicyclic cores from the very same starting materials by introducing organocatalysts
with different activation modes in the reaction are presented.
Key words
1,3-dicarbonyls - heterocycles - Michael addition - multicomponent reaction - organocatalysis
