A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes.
Emily KissCraig D CampbellRussell W DriverJohn D JolliffeRosemary LangTetiana SergeievaSergiy I OkovytyyRobert S PatonMartin D SmithPublished in: Angewandte Chemie (International ed. in English) (2016)
An approach to the intramolecular Diels-Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocenters with complete stereocontrol. Computational analysis reveals that the reaction proceeds by a Michael/Michael/cyclopropanation/epimerization cascade in which size and coordination of the counterion is key.
Keyphrases