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Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters.

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.

SUBMITTER: Li Z

PROVIDER: S-EPMC8442720 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Organocatalytic asymmetric formal oxidative coupling for the construction of all-aryl quaternary stereocenters.

Li Zhiyang Z Li Yichen Y Li Xingguang X Wu Mandi M He Ming-Liang ML Sun Jianwei J

Chemical science 20210729 35

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-di ...[more]

PMID: 34659717

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