A Counterion‐Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes

• DOI: 10.1002/ange.201608534
• Publication Date: 2016-10-13T03:17:08Z
• Authors: Emily Kiss; Craig D. Campbell; Russell W. Driver; John D. Jolliffe; Rosemary Lang; Tetiana Sergeieva; Sergiy Okovytyy; Robert S. Paton; Martin D. Smith
• Keywords: 01 natural sciences; Communications; 0104 chemical sciences

AbstractAn 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.