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

Asymmetric aerobic decarboxylative Povarov reactions of N-aryl α-amino acids with methylenephthalimidines via cooperative photoredox and chiral Brønsted acid catalysis.
Chem Commun (Camb). 2019 Oct 11;:
Authors: Li J, Gu Z, Zhao X, Qiao B, Jiang Z
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).
PMID: 31603445 [PubMed - as supplied by publisher]

Source: Chemical Communications - October 10, 2019 Category: Chemistry Authors: Li J, Gu Z, Zhao X, Qiao B, Jiang Z Tags: Chem Commun (Camb) Source Type: research