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Chiral-Anion-Mediated Asymmetric Heck-Matsuda Reaction of Acyclic Alkenyl Alcohols

Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen and Zhi-Yong Han*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email:

T. Zhang, W.-A. Li, H.-C. Shen, S.-S. Chen, Z.-Y. Han, Org. Lett., 2021, 23, 1473-1477.

DOI: 10.1021/acs.orglett.1c00152

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Chiral anion phase transfer enables an asymmetric Heck-Matsuda reaction of acyclic alkenyl alcohols to provide various chiral ketones in high levels of enantioselectivity. A catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial to suppress palladium-hydride-mediated side reactions.

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proposed mechanism

Key Words

Heck reaction, arylation

ID: J54-Y2021