Abstract
The deployment of fluorinated functional groups has become a widespread tool in medicinal chemistry due to the impact of fluorine on lipophilicity and metabolic stability. Among these compounds, enantiopure secondary trifluoromethylcarbinols are recurrent features in bioactive compounds. Herein, we present a diastereoselective redox-neutral process allowing the stereospecific synthesis of 1,5-carboxamido-trifluoromethylcarbinols through the formal reduction of a trifluoromethylketone into a trifluoromethylcarbinol. A combined experimental and computational investigation unveiled a network of interconnected equilibria leading to a key hydride transfer event.
Original language | English |
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Pages (from-to) | 15751-15756 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 15 |
Issue number | 38 |
Early online date | 9 Sep 2024 |
DOIs | |
Publication status | Published - 9 Sep 2024 |
Austrian Fields of Science 2012
- 104015 Organic chemistry