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

Jian Zhang; Chen Guo; Weijun Tang; Dong Xue; Huaming Sun; Jianliang Xiao; Chao Wang

doi:10.1055/a-2295-5417

Synthesis, Table of Contents

Synthesis 2024; 56(22): 3390-3398
DOI: 10.1055/a-2295-5417

paper

Dual Catalysis

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

Authors

Jian Zhang‡

^aKey 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‡

^aKey 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

^aKey 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

^aKey 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

^aKey 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

^bDepartment of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK
Chao Wang∗

^aKey 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

Abstract

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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

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References

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Supplementary Material

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