Abstract
Palladium-catalyzed reactions of alkenyl nonaflates 1, 2, and 3 derived from 8-oxabicyclo[3.2.1]octan-3-ones with bis(pinacolato)diboron as coupling partner led to bicyclic boronic esters 4, 5, and 6, respectively. They were further transformed in a subsequent coupling step either using iodobenzene or a second equivalent of the corresponding bicyclic alkenyl nonaflate. Products 7 and 10 were obtained in reasonable to fair yields. Applying this method to N-carbethoxytropinone derived nonaflate 11 provided an epibatidine-atropine hybrid 13 in only three steps with 65% overall yield.
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