Catalytic Asymmetric Homologation of 4‐Substituted Cyclohexanones with CF<sub>3</sub>CHN<sub>2</sub>: Enantioselective Synthesis of α<i>‐</i>Trifluoromethyl Cycloheptanones
Shu‐Sen Li, Shuo Sun, Jianbo Wang
Abstract
Abstract Introduction of the trifluoromethyl group (CF 3 ) into organic molecules in an enantioselective manner has attracted significant attention, but still remains a challenging problem. We herein report a catalytic asymmetric trifluoromethylation of cyclic ketones via a Sc III /chiral bisoxazoline‐catalyzed homologation reaction by employing 2,2,2‐trifluorodiazoethane (CF 3 CHN 2 ) as the CF 3 source. This desymmetrization process is highly efficient and generates two chiral centers with excellent diastereoselectivity and enantioselectivity, affording chiral α ‐trifluoromethyl cyclic ketones in a straightforward manner.
Topics & Concepts
Enantioselective synthesisTrifluoromethylCatalysisChemistryStereochemistryOrganic chemistryAlkylFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsCarbohydrate Chemistry and Synthesis