An Environmentally Sustainable Synthesis of Enantioenriched CF3‐Chromanol, Indanol and Tetralol Derivatives by Rh‐Catalyzed Asymmetric Transfer Hydrogenation

• Published in: ChemCatChem Vol. 14; no. 15
• Main Authors: Molina Betancourt, Ricardo, Bacheley, Lucas, Karapetyan, Anzhela, Guillamot, Gérard, Phansavath, Phannarath, Ratovelomanana‐Vidal, Virginie
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 05-08-2022
• Subjects: Alcohols; asymmetric transfer hydrogenation; Asymmetry; catalysis; green chemistry; Hydrogenation; Ketones; rhodium; trifluoromethyl
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.202200595

The Rh(III)‐catalyzed asymmetric reduction of α‐trifluoromethyl ketones through transfer hydrogenation was developed under mild conditions to access a series of enantioenriched cis‐trifluoromethyl alcohols via a dynamic kinetic resolution process. The reaction was efficiently performed in the green solvent 2‐MeTHF with HCO2H/Et3N (1 : 1) as the hydrogen source. High yields, alongside excellent diastereo‐ and enantioselectivities were obtained for the synthesis of CF3‐chromanol, CF3‐indanol and CF3‐tetralol derivatives.
Rhodium(III)‐catalyzed asymmetric reduction of α‐trifluoromethyl ketones through transfer hydrogenation is reported in the green solvent 2‐MeTHF with HCO2H/Et3N (1 : 1) as the hydrogen source to access enantioenriched cis‐trifluoromethyl alcohols via a dynamic kinetic resolution process. High yields, alongside excellent diastereo‐ and enantioselectivities were obtained for the synthesis of CF3‐chromanol, CF3‐indanol and CF3‐tetralol derivatives.