Radical changes in Lewis acid catalysis

• Verfasst von: Bleith, Tim Manuel [VerfasserIn]
• Verfasst von: Deng, Qing-Hai [VerfasserIn]
• Verfasst von: Wadepohl, Hubert [VerfasserIn]
• Verfasst von: Gade, Lutz H. [VerfasserIn]
• Titel: Radical changes in Lewis acid catalysis
• Titelzusatz: matching metal and substrate
• Verf.angabe: Tim Bleith, Qing-Hai Deng, Hubert Wadepohl, and Lutz H. Gade
• E-Jahr: 2016
• Jahr: 02 June 2016
• Umfang: 5 S.
• Fussnoten: Gesehen am 15.12.2022
• Titel Quelle: Enthalten in: Angewandte Chemie
• Ort Quelle: Weinheim : Wiley-VCH, 1887
• Jahr Quelle: 2016
• Band/Heft Quelle: 128(2016), 27, Seite 7983-7987
• ISSN Quelle: 1521-3757
• DOI: doi:10.1002/ange.201603072
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Enantioselektive Katalyse
• Sach-SW: Kupfer
• Sach-SW: Radikalreaktionen
• Sach-SW: Reaktionsmechanismen
• Sach-SW: Zink
• K10plus-PPN: 1827169028

Abstract

Whereas the stereochemical rigidity of the coordination sphere of boxmi/CuII catalysts is key to achieving high enantioselectivity in the electrophilic alkylation of β-ketoesters, this pathway is outperformed by a radical process for the corresponding catalytic transformation of oxindoles, giving rise to racemic products. For the corresponding ZnII catalysts, the selectivity in the latter process is outstanding despite the greater plasticity of the coordination shell. This reaction was thus developed into a highly useful synthetic method, which enabled the conversion of wide range of substrates with high yields and enantioselectivities.