Diastereoselective synthesis of highly substituted tetrahydroquinolines using benzoylacetonitrile via aza Diels–Alder reaction

Abstract

Diastereoselective aza-Diels–Alder reaction between in situ generated 2-aminophenyl-substituted enones and α-cyano-α,β-unsaturated aromatic ketone has been developed. In the presence of TEA as a catalyst prepared highly substituted tetrahydroquinolines with an all-carbon quaternary center in an in situ fashion. Both tetrahydroquinoline isomers (exo and endo) with excellent diastereoselectivity and high yields were synthesized in very mild conditions.