Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
Org Biomol Chem. 2022 Sep 28;20(37):7503-7518. doi: 10.1039/d2ob01459a.
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.
我们描述了一种简便操作、高产率的方法，通过直接的合成路线，在手性控制下制备新型磺酰基并苯并[4.2.1]壬烷氟代氧杂双环[4.2.1]壬烷，包括（i）NaBH 介导的磺酰基 3-亚甲基-氧杂苯并环辛-6-酮还原和（ii）BF·OEt 介导的分子内亲核氟环化。提出并讨论了制备的可能机制。该方案可以在短时间内温和条件下轻松地在桥接头位置上安装氟原子，导致一个碳-碳和一个碳-氟键的形成。
