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A Counterion‐Directed Approach to the Diels–Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes |
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| Authors: | Dr Emily Kiss Dr Craig D Campbell Dr Russell W Driver John D Jolliffe Rosemary Lang Dr Tetiana Sergeieva Prof Dr Sergiy Okovytyy Prof Dr Robert S Paton Prof Dr Martin D Smith |
| Institution: | 1. http://msmith.chem.ox.ac.uk/;2. Chemistry Research Laboratory, University of Oxford, Oxford, UK;3. Department of Chemistry, Dnipropetrovsk National University, Dnipropetrovsk, Ukraine |
| Abstract: | 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. |
| Keywords: | cations cycloadditions diastereoselectivity density-functional calculations heterocycles |