A highly diastereoselective synthesis of deep molecular baskets
Zhiquan Lei1, Michael J Gunther1, Vageesha W Liyana Gunawardana1
1Department of Chemistry & Biochemistry, The Ohio State University, 100 West 18th Avenue, 43210 Columbus, Ohio, USA. badjic.1@osu.edu.
Abstract:
We describe a preparative method for directing Mizoroki-Heck cyclotrimerization of enantioenriched bromonorbornenes into molecular baskets having increasingly deeper and extendable aromatic cavities. Such diastereoselective cyclotrimerizations of the bromo-olefinic substrates resulted from prevalent β migratory insertions without the formation of palladacycle intermediate(s). The facile access to multigram quantity of a new series of basket-like hosts clears the way for creating novel supramolecular materials for storage, sequestration and catalysis.
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