Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp<sup>3</sup>)–H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds
Long‐Tao Huang, Seiya Fukagawa, M. Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Abstract
The enantioselective C–H alkylation of 8-ethylquinolines with enones or acrolein using a RhIII catalyst and a chiral carboxylic acid is described. Under mild reaction conditions, a binaphthyl-based chiral carboxylic acid enables the enantioselective cleavage of the 8-ethylquinoline C(sp3)–H bond. The obtained results demonstrate the utility of the combination of a high-valent group 9 metal catalyst and a chiral carboxylic acid for the enantioselective C(sp3)–H activation and the subsequent C–C bond formation.
Topics & Concepts
Enantioselective synthesisChemistryRhodiumCarboxylic acidAlkylationCatalysisAcroleinBond cleavageMedicinal chemistryOrganic chemistryStereochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis