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Synthesis of Tetrahydropyridazines by a Metal–Carbene-Directed Enantioselective Vinylogous N[BOND]H Insertion/Lewis Acid-Catalyzed Diastereoselective Mannich Addition


  • Support for this research to M.P.D. from the National Institutes of Health (GM 46503) is gratefully acknowledged.


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A versatile cascade of reactions, triggered by RhII-catalyzed diazo decomposition followed by a vinylogous N[BOND]H insertion/Lewis acid catalyzed Mannich addition, that produces highly substituted 1,2,3,6-tetrahydropyridazines in up to 97 % ee with high yield and diastereocontrol has been developed.