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
a   Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
b   School of Chemical Science, University of Chinese Academy of Sciences, Beijing 100490, P. R. of China
,
Qi Yang
c   Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
,
Sanzhong Luo
a   Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
c   Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
› Author Affiliations
We thank the Natural Science Foundation of China (21672217, 21861132003, and 22031006) and Tsinghua University Initiative Scientific Research Program for financial support. S.L. is supported by the National Program of Top-notch Young Professionals.


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.

Supporting Information



Publication History

Received: 21 February 2021

Accepted after revision: 24 March 2021

Accepted Manuscript online:
24 March 2021

Article published online:
19 April 2021

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