NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2<i>H</i>)-ones and Isoquinolines
Debabrata Barman, Tanmoy Kumar Ghosh, Krishanu Show, Sudipto Debnath, Tapas Ghosh, Dilip K. Maiti
Abstract
N-Heterocyclic carbene-catalyzed tandem Stetter-aldol reaction of phthalaldehyde and α,β-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.
Topics & Concepts
Aldol reactionAnnulationChemistryDominoAldimineIsoquinolineCascade reactionOrganic chemistryCombinatorial chemistryStereochemistryCatalysisN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods