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Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids

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Abstract

Kinetic resolution of [2.2]paracyclophane aldimines was achieved through palladium-catalyzed enantioselective arylation with arylboronic acids. The catalytic process provided reliable access to enantiopure paracyclophane derivatives with planar and central chirality as well as the recovered chiral aldimines with a selectivity factor up to 368. Furthermore, the synthetic utility of the [2.2]paracyclophane aldimines has been demonstrated by converting them into useful chiral building blocks.

Graphical abstract: Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids

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Publication details

The article was received on 13 Aug 2019, accepted on 26 Oct 2019 and first published on 28 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01011D
Org. Chem. Front., 2019, Advance Article

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    Synthesis of paracyclophanes with planar and central chirality: kinetic resolution of [2.2]paracyclophane aldimines via palladium-catalyzed addition of arylboronic acids

    Y. Zhao, H. Wang, B. Wu and Y. Zhou, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01011D

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