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Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation.

ABSTRACT: The simultaneous construction of two different chiralities via a simple operation poses considerable challenge. Herein a cationic gold-catalyzed asymmetric hydroarylation of ortho-alkynylaryl ferrocenes derivatives is developed, which enable the simultaneous construction of axial and planar chirality. The here identified TY-Phos derived gold complex is responsible for the high yield, good diastereoselectivity (>20:1 dr), high enantioselectivities (up to 99% ee) and mild conditions. The catalyst system also shows potential application in the synthesis of chiral biaryl compounds. The cause of high enantioselectivity of this hydroarylation is investigated with density functional theory caculation.

SUBMITTER: Zhang PC

PROVIDER: S-EPMC8322429 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation.

Zhang Pei-Chao PC Li Yin-Lin YL He Jiafeng J Wu Hai-Hong HH Li Zhiming Z Zhang Junliang J

Nature communications 20210729 1

The simultaneous construction of two different chiralities via a simple operation poses considerable challenge. Herein a cationic gold-catalyzed asymmetric hydroarylation of ortho-alkynylaryl ferrocenes derivatives is developed, which enable the simultaneous construction of axial and planar chirality. The here identified TY-Phos derived gold complex is responsible for the high yield, good diastereoselectivity (>20:1 dr), high enantioselectivities (up to 99% ee) and mild conditions. The catalyst ...[more]

PMID: 34326337

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