We describe a facile-operational, high-yield method for the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes by a straightforward synthetic route, including (i) NaBH-mediated reduction of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones and (ii) BF·OEt-mediated intramolecular nucleophilic fluorocyclization. The plausible mechanism for the preparation is proposed and discussed. This protocol can easily install a fluoro-atom on the bridged head position in a short time and under mild conditions, resulting in one carbon-carbon and one carbon-fluorine bond formation.
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| http://dx.doi.org/10.1039/d2ob01459a | DOI Listing |
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