Three‐Component Triple Organocascade Synthesis of Hexahydropyridazine Derivatives via a Sequential Michael/Amination/Cyclization Reaction

Abstract

AbstractThe organocatalytic asymmetric synthesis of hexahydropyridazines were performed through a unique Michael/amination/cyclization reaction. The organocascade reaction proceeded smoothly between 2‐arylidene‐1,3‐indandiones and aldehydes followed by the addition of azodicarboxylates catalyzed by the privileged organocatalyst α,‐α‐L‐diphenylprolinol trimethylsilyl ether (10 mol%) in the presence of a base additive Et3N (20 mo%) at 0 °C. A series of substituted hexahydropyridazines were obtained in good to high chemical yields (55–78 %) and reasonable to high levels of stereoselectivities (51–93 % ee and 4 : 1 d.r.).