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Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions


Transannular Diels-Alder (TADA) reactions are a powerful tool for the construction of polycyclic structures with four stereogenic centers. A series of remarkably facile and stereoselective TADA reactions was observed experimentally by Merlic and coworkers. In this thesis, the mechanism was modeled quantum mechanically and the controlling factors of the high stereoselectivity and reactivity of TADA were determined for these reactions and the analogous bimolecular and intramolecular Diels-Alder reactions.

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