Synthesis 2023; 55(14): 2228-2240
DOI: 10.1055/s-0041-1738435
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

Copper(I)-Catalyzed Enantioselective 1,4-Conjugate Hydrophos­phination of α,β-Unsaturated Esters

Ye Wang
a   College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, Sichuan 610068, P. R. of China
b   CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
,
Zi-Qing Wang
b   CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
,
Liang Yin
b   CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author Affiliations
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 22271302), the Science and Technology Commission of Shanghai Municipality (No. 20JC1417100 and No. 21XD1424800), the Key Laboratory of Synthetic Chemistry of Natural Substances, CAS, and Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.


Abstract

A copper-catalyzed enantioselective 1,4-conjugate hydrophosphination is achieved by employing α,β-unsaturated esters as electrophiles and diarylphosphines as pronucleophiles. An array of chiral phosphines was prepared in high to excellent enantioselectivity. Moreover, a triple catalytic symmetric conjugate hydrophosphination occurred smoothly to afford the product.

Supporting Information



Publication History

Received: 13 February 2023

Accepted after revision: 17 March 2023

Article published online:
17 April 2023

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