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

Pei-Chao Zhang; Yin-Lin Li; Jiafeng He; Hai-Hong Wu; Zhiming Li; Junliang Zhang

doi:10.1038/s41467-021-24678-5

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

Nat Commun. 2021 Jul 29;12(1):4609. doi: 10.1038/s41467-021-24678-5.

Authors

Pei-Chao Zhang¹, Yin-Lin Li¹, Jiafeng He¹, Hai-Hong Wu², Zhiming Li³, Junliang Zhang^{4

5}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China.
² Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China. hhwu@chem.ecnu.edu.cn.
³ Department of Chemistry, Fudan University, Shanghai, China. lizm@fudan.edu.cn.
⁴ Department of Chemistry, Fudan University, Shanghai, China. junliangzhang@fudan.edu.cn.
⁵ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, China. junliangzhang@fudan.edu.cn.

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.

Grants and funding

22031004/National Natural Science Foundation of China (National Science Foundation of China)