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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.0c02872 |