Iridium-Catalyzed Asymmetric Transfer Hydrogenation of 1-Aryl-1-alkylethenes with Ethanol

Xixia Tang, Lu Qian, Guixia Liu* and Zheng Huang*

*Shanghai Institute of Organic Chemistry, University of CAS, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: guixiasioc.ac.cn, huangzhsioc.ac.cn

X. Tang, L. Qian, G. Liu, Z. Huang, Org. Lett., 2023, 25, 4950-4954.

DOI: 10.1021/acs.orglett.3c01880

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Abstract

A chiral (PCN)Ir complex catalyzes an asymmetric transfer hydrogenation of 1-aryl-1-alkylethenes with ethanol. The reaction offers high enantioselectivities, good functional group tolerance, and operational simplicity. A formal intramolecular asymmetric transfer hydrogenation of alkenols without an external H-donor, producing a tertiary stereocenter and remote ketone group simultaneously.

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Iridium-Catalyzed Enantioselective Transfer Hydrogenation of 1,1-Dialkylethenes with Ethanol: Scope and Mechanism

L. Qian, C. Yu, L. Gan, X. Tang, Y. Wang, G. Liu, X. Leng, Z. Sun, Y. Guo, X.-S. Xue, Z. Huang, J. Am. Chem. Soc., 2024, 146, 3427-3437.

Chiral Iridium Complexes of Anionic NCP Pincer Ligand for Asymmetric Transfer Hydrogenation of 1,1-Diarylethenes with Ethanol

L. Qian, X. Tang, Z. Huang, Y. Wang, G. Liu, Z. Huang, Org. Lett., 2021, 23, 8978-8983.

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Key Words

reduction of alkenes, ethanol

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ID: J54-Y2023