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Keywords:

  • asymmetric organocatalysis;
  • aza-Diels-Alder;
  • O-Michael addition;
  • hemiaminal;
  • pyrano[2,3-b]pyridines

Abstract

An asymmetric aza-Diels-Alder and O-Michael addition sequence has been developed to construct chiral hydropyrano[2,3-b]pyridine derivatives with good yields and excellent stereoselectivity, by starting with N-Ts-1-aza-1,3-butadienes and aliphatic aldehydes tethered to an α,β-unsaturated ketone motif. A tandem O-Michael addition reaction was completed via acid catalysis.