Anti-Diastereoselective Synthesis of CF3-Containing Spirooxazolines and Spirooxazines via Regiospecific Trifluoromethylative Spirocyclization by Photoredox Catalysis

作者：Noto Naoki; Miyazawa Kazuki; Koike Takashi^*; Akita Munetaka

来源：Organic Letters, 2015, 17(15): 3710-3713.

DOI：10.1021/acs.orglett.5b01694

A novel synthesis of CF3-containing spirooxazolines and spirooxazines has been developed. Regiospecific trifluoromethylative spirocyclization (CF3-spirocyclization) of cyclic alkenes bearing an amide pendant mediated by photoredox catalysis is a useful strategy for construction of a C(sp(3))-CF3 bond and an spirooxazoline or spirooxazine ring onto C = C bonds via a single step. The key intermediate is alpha-CF3-substituted carbocationic species smoothly generated from single-electron-transfer (SET) photoredox processes, which results in diastereoselective spirocyclization. This is the first example of synthesis of CF3-containing spirooxazolines and spirooxazines in anti-fashion with respect to the CF3 group and the oxygen atom of the spirocycles.

• 出版日期2015-8-7