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Catalytic Asymmetric Transfer Hydrogenation of trans-Chalcone Derivatives Using BINOL-derived Boro-phosphates

Fei Na, Susana S. Lopez, Alice Beauseigneur, Lucas W. Hernandez, Zhuoxin Sun and Jon C. Antilla*

*Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email: jantillatju.edu.cn

F. Na, S. S. Lopez, A. Beauseigneur, L. W. Hernandez, Z. Sun, J. C. Antilla, Org. Lett., 2020, 22, 5953-5957.

DOI: 10.1021/acs.orglett.0c02042


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Abstract

A chiral phosphoric acid catalyzes an asymmetric transfer hydrogenation of trans-chalcones in the presence of pinacolborane as hydride source. This methodology provides chiral dihydrochalcone derivatives in high yields and with high enantioselectivities under mild conditions.

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proposed mechanism



Key Words

1,4-Reduction of α,β-unsaturated compounds, pinacolborane, organocatalysis


ID: J54-Y2020