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SCpRh(III)-Catalyzed Asymmetric C–H Trifluoromethylalkylation of <i>N</i>-Methoxybenzamides with <i>β-</i>Trifluoromethyl-α,β-Unsaturated Ketones

Zhuo Wu, Muzi Li, Qing Gu, Shu‐Li You

2024Organic Letters10 citationsDOI

Abstract

Asymmetric C–H trifluoromethylalkylation represents a novel and straightforward synthetic method for the construction of chiral CF 3 -containing compounds. However, the reported examples remain limited, given the challenges of reactivity and enantioselective control. Herein, we report a SCpRh(III)-catalyzed asymmetric aryl and alkenyl C–H trifluoromethylalkylation reaction with β-trifluoromethyl-α,β-unsaturated ketones. The chiral CF 3 -bearing adducts were obtained in moderate to good yields with high enantioselectivity (up to 81% yield and 96% ee). The reaction features mild conditions and broad substrate scope. The chiral CF 3 -bearing products could undergo diverse functional group transformations.

Topics & Concepts

TrifluoromethylChemistryEnantioselective synthesisSubstrate (aquarium)Yield (engineering)AdductCatalysisArylReactivity (psychology)Medicinal chemistryStereochemistryOrganic chemistryOceanographyGeologyAlkylPathologyAlternative medicineMetallurgyMedicineMaterials scienceFluorine in Organic ChemistryInorganic Fluorides and Related Compounds
SCpRh(III)-Catalyzed Asymmetric C–H Trifluoromethylalkylation of <i>N</i>-Methoxybenzamides with <i>β-</i>Trifluoromethyl-α,β-Unsaturated Ketones | Litcius