Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp3)–H Alkylation of 8‑Ethylquinolines with α,β-Unsaturated Carbonyl Compounds

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. T...

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Veröffentlicht in:Organic letters 2020-11, Vol.22 (21), p.8256-8260
Hauptverfasser: Huang, Long-Tao, Fukagawa, Seiya, Kojima, Masahiro, Yoshino, Tatsuhiko, Matsunaga, Shigeki
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02872