Abstract
AbstractDisclosed here an amine‐catalyzed reductive aldol‐condensation followed by an intramolecular reductive Michael‐addition cascade employing Hantzsch ester as hydride source to a keto‐bis‐enone to provide enantio‐ and diastereoselective benzannulated diquinanes having three consecutive stereocenters, one of which is an all‐carbon quaternary formyl stereocenter. Interestingly, on changing a tether connecting the ketone and an enone moiety from an aliphatic to an aromatic, a change in reactivity is observed. In this case, instead of the above‐mentioned reductive aldol condensation, an asymmetric aldol reaction occurs, followed by an iminium/enamine isomerization and, finally diastereoselective Michael addition reaction occurs. As a result, a bis‐benzannulated diquinane is obtained with vicinal congested quaternary chiral centers.
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