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Asymmetric aerobic decarboxylative Povarov reactions of N-aryl α-amino acids with methylenephthalimidines via cooperative photoredox and chiral Brønsted acid catalysis

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Abstract

An enantioselective aerobic decarboxylative Povarov reaction of N-aryl α-amino acids with methylenephthalimidines through cooperative photoredox and chiral Brønsted acid catalysis is reported. With a transition metal-free dual catalytic system including a chiral phosphoric acid and DPZ as a photosensitizer mediated by visible light, the transformations provided a series of valuable chiral isoindolin-1-ones containing a 3,3-spiro-tetrahydroquinoline-based stereocenter in high yields (up to 83%) with good to excellent enantioselectivities (up to 98% ee) and excellent diastereoselectivity (>20 : 1 dr).

Graphical abstract: Asymmetric aerobic decarboxylative Povarov reactions of N-aryl α-amino acids with methylenephthalimidines via cooperative photoredox and chiral Brønsted acid catalysis

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Publication details

The article was received on 19 Sep 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07380A
Chem. Commun., 2019, Advance Article

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    Asymmetric aerobic decarboxylative Povarov reactions of N-aryl α-amino acids with methylenephthalimidines via cooperative photoredox and chiral Brønsted acid catalysis

    J. Li, Z. Gu, X. Zhao, B. Qiao and Z. Jiang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07380A

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