Merging the Non‐Natural Catalytic Activity of Lipase and Electrosynthesis: Asymmetric Oxidative Cross‐Coupling of Secondary Amines with Ketones

We describe the enantioselective oxidative cross‐coupling of secondary amines with ketones by combining the non‐natural catalytic activity of lipase with electrosynthesis. Various 2,2‐disubstituted 3‐carbonyl indoles with a stereogenic quaternary carbon center were synthesized from 2‐substituted ind...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-07, Vol.61 (30), p.e202203666-n/a
Main Authors: Long, Chao‐Jiu, Cao, Huan, Zhao, Ben‐Kun, Tan, Yu‐Fang, He, Yan‐Hong, Huang, Chu‐Sheng, Guan, Zhi
Format: Article
Language:English
Subjects:
Amines
Asymmetric Catalysis
Carbonyl compounds
Carbonyls
Catalysis
Catalytic activity
Cross coupling
Electrochemistry
Enantiomers
Enzymatic Electrosynthesis
Hydrolase
Indoles
Ketones
Lipase
Organic solvents
Oxidative Cross-Coupling
Stereoselectivity
Substrates
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Summary:We describe the enantioselective oxidative cross‐coupling of secondary amines with ketones by combining the non‐natural catalytic activity of lipase with electrosynthesis. Various 2,2‐disubstituted 3‐carbonyl indoles with a stereogenic quaternary carbon center were synthesized from 2‐substituted indoles in yields up to 78 % with good enantio‐ and diastereoselectivities (up to 96 : 4 e.r. and >20 : 1 d.r.). This unprecedented protocol demonstrated that hydrolase catalysis is compatible with electrosynthesis, and the reaction can be carried out in organic solvents with a broad substrate scope and good stereoselectivity. This work provides insights into enzymatic electrosynthesis. An asymmetric oxidative cross‐coupling strategy that combines the non‐natural catalytic activity of lipase with organic electrosynthesis was developed. This unprecedented protocol demonstrates that hydrolase catalysis is compatible with electrosynthesis.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202203666