Asymmetric Reduction of Aromatic α-Dehydroamino Acid Esters with Water as Hydrogen Source

Yuze Dai, Jingchao Chen*, Zheting Wang, Ting Wang, Lin Wang, Yong Yang, Xingfang Qiao and Baomin Fan*

*Yunnan Minzu University, Kunming 650504, Yunnan, China, Email: chenjingchao84163.com, adams.bmfhotmail.com

Y. Dai, J. Chen, Z. Wang, T. Wang, L. Wang, Y. Yang, X. Qiao, B. Fan, J. Org. Chem., 2021, 86, 7141-7147.

DOI: 10.1021/acs.joc.1c00426

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Abstract

A Rh/Cu co-catalytic system enables an asymmetric reduction of aromatic α-dehydroamino acid esters with water as the hydrogen source to provide chiral α-amino acid esters. The reaction tolerates various functional groups and provides access to chiral deuterated α-amino esters by using D₂O.

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Key Words

reduction of allkenes, reduction of α,β-unsaturated compounds, reduction of enamines, zinc

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ID: J42-Y2021