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Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters† † Electronic supplementary information (ESI) available. See DOI: 10.1039/d1sc03324g

ABSTRACT: A new catalytic asymmetric formal cross dehydrogenative coupling process for the construction of all-aryl quaternary stereocenters is disclosed, which provides access to rarely explored chiral tetraarylmethanes with excellent enantioselectivity. The suitable oxidation conditions and the hydrogen-bond-based organocatalysis have enabled efficient intermolecular C–C bond formation in an overwhelmingly crowded environment under mild conditions. para-Quinone methides bearing an ortho-directing group serve as the key intermediate. The precise loading of DDQ is critical to the high enantioselectivity. The chiral products have also been demonstrated as promising antiviral agents. A one-pot oxidation of racemic triarylmethanes to form para-quinone methides followed by enantioselective construction of all-aryl quaternary stereocenters has been developed.

SUBMITTER: Li Z

PROVIDER: S-EPMC8442720 | biostudies-literature |

REPOSITORIES: biostudies-literature

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