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

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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… Click to show full abstract

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.

Keywords: aza diels; alder reaction; highly substituted; diels alder; substituted tetrahydroquinolines

Journal Title: Tetrahedron Letters
Year Published: 2021

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