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Radical Fluorosulfonylation/Double Diels-Alder Sequence to Access Tricyclo[3.2.1.02,7]octanes
Hui Liang1, Shengchun Hu2, Shuai Shi1
1National Key Laboratory for the Development and Utilization of Forest Food Resources, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China.
Abstract:
A cascade strategy for the rapid construction of tricyclo[3.2.1.02,7]octanes is reported. This one-pot, two-step sequence can be efficiently accomplished by utilizing readily available propargylic alcohols as the starting materials and FSO2Cl as the fluorosulfonyl radical precursor. The FSO2-functionalized tricyclooctane products, bearing multiple reactive sites, are poised for postderivatizations. Based on mechanism studies, a cascade sequence involving radical hydro-fluorosulfonylation, dehydration, and a double Diels-Alder reaction has been proposed.
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