Copper‐Catalyzed α‐Carbamoylation of Cyclic β‐Ketoesters

A copper‐catalyzed, base‐free α‐carbamoylation of cyclic β‐ketoesters with isocyanates has been developed. While conventional base‐promoted methods suffer from a spontaneous intramolecular rearrangement that leads to undesired imides, this protocol utilizes a Cu(OTf) 2 /bisoxazoline (BOX) catalytic system to effectively suppress the rearrangement pathway. The reaction provides efficient access to various α‐substituted β,β′‐dicarbonyl amides bearing an all‐carbon quaternary center in high yields with a broad substrate scope and excellent functional group tolerance.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-08-03
DOI
https://doi.org/10.1002/ejoc.70739
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
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article

Copper‐Catalyzed α‐Carbamoylation of Cyclic β‐Ketoesters

Akihiro Sakama, Kazuaki Kudo, Yihao Shi
European Journal of Organic Chemistry
Carbon dioxide utilization in catalysis
article

Copper‐Catalyzed α‐Carbamoylation of Cyclic β‐Ketoesters

Akihiro Sakama, Kazuaki Kudo, Yihao Shi
article en

Abstract

A copper‐catalyzed, base‐free α‐carbamoylation of cyclic β‐ketoesters with isocyanates has been developed. While conventional base‐promoted methods suffer from a spontaneous intramolecular rearrangement that leads to undesired imides, this protocol utilizes a Cu(OTf) 2 /bisoxazoline (BOX) catalytic system to effectively suppress the rearrangement pathway. The reaction provides efficient access to various α‐substituted β,β′‐dicarbonyl amides bearing an all‐carbon quaternary center in high yields with a broad substrate scope and excellent functional group tolerance.

European Journal of Organic Chemistry
The University of Tokyo (JP)
Openalex Percentile: Top 20%
Carbon dioxide utilization in catalysis
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