Journal
ORGANIC LETTERS
Volume 17, Issue 15, Pages 3710-3713Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01694
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Funding
- JSPS KAKENHI [26288045, 15K13689]
- Naito Foundation
- Grants-in-Aid for Scientific Research [15K13689, 26288045] Funding Source: KAKEN
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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.
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