Intramolecular conjugate addition reactions of amines and carbamates to 2,5-cyclohexadien-1-ones: Stereoselective synthesis of perhydroindoles

Article abstract of DOI:10.1016/S0040-4020(99)00455-X

Intramolecular conjugate addition reactions of 4,4-disubstituted-2,5- cyclohexadien-1-ones are described within the context of possible approaches to manzamine A. Amine 4 provided tricycle 6, with improper relative stereochemistry for use in an approach to manzamine A. Carbamates 25 and 38 gave perhydroindoles 26 and 28 b under conditions of thermodynamic control, respectively, with the proper relative stereochemistry required for manzamine A. Carbamate 25 gave diastereomeric perhydroindole 27 under conditions of thermodynamic control.