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Synthesis
DOI: 10.1055/a-2295-5417
paper
Dual Catalysis

Asymmetric Hydrogenative Coupling of Indoles with Unsaturated Ketones Enabled by Copper/Ruthenium Relay Catalysis

Jian Zhang‡
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
,
Chen Guo‡
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
,
Weijun Tang 
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
,
Dong Xue
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
,
Huaming Sun
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
,
Jianliang Xiao
b   Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK
,
Chao Wang∗
a   Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, P. R. of China
› Author AffiliationsThis research was supported by the National Natural Science Foundation of China (22172096), the Fundamental Research Funds for the Central Universities (GK202307002, GK202002003), the Projects for the Academic Leaders and Academic Backbones, Shaanxi Normal University (16QNGG008), the Natural Science Basic Research Program of Shaanxi Province (2021JC-30), and the 111 project (B14041).
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Abstract

A relay catalytic system is developed for the asymmetric hydrogenative coupling of indoles with α,β-unsaturated ketones, affording enantioenriched chiral γ-indole alcohols with broad substrate scope and excellent enantioselectivities (32 examples, up to >99% ee). Mechanistic studies suggest that the relay catalytic system consists of copper-catalyzed alkylation and ruthenium-catalyzed asymmetric hydrogenation.

Key words

relay catalysis - indole - unsaturated ketone - chiral alcohol - C–C bond formation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2295-5417.
  • Supporting Information


Publication History

Received: 01 March 2024

Accepted after revision: 26 March 2024

Accepted Manuscript online:
26 March 2024

Article published online:
03 April 2024

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