Photoredox-Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Zongbin Jia; Qi Yang; Sanzhong Luo

doi:10.1055/a-1463-4219

Synthesis, Table of Contents

Synthesis 2021; 53(16): 2809-2818
DOI: 10.1055/a-1463-4219

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Photoredox-Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Zongbin Jia

^aKey Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^bSchool of Chemical Science, University of Chinese Academy of Sciences, Beijing 100490, P. R. of China

,

Qi Yang

^cCenter of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

,

Sanzhong Luo∗

^aKey Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China

^cCenter of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China

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Abstract

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Abstract

A catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis is reported. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, followed by isomerization, leading to aza-Morita–Baylis–Hillman-type products with good diastereo- and enantioselectivity.

Key words

cross dehydrogenative coupling - photoredox oxidation - primary amine catalysis - dienamine - enone

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References

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