BifunctionalNHC-Catalyzed Asymmetric IntramolecularConjugate Addition via Noncovalent Interaction

Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic and nucleophilic centers of substrates, the reaction proceeds through a well-organized transition state, thereby affording products with up to 94% ee and a broad scope. The process is found to be scalable. The initial mechanistic study supports the bifunctional nature of the newly designed NHC.

Publication Details

Journal
Figshare
Published
2025-02-28
DOI
https://doi.org/10.1021/acs.orglett.5c00315.s001
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
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BifunctionalNHC-Catalyzed Asymmetric IntramolecularConjugate Addition via Noncovalent Interaction

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N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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BifunctionalNHC-Catalyzed Asymmetric IntramolecularConjugate Addition via Noncovalent Interaction

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Abstract

Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic and nucleophilic centers of substrates, the reaction proceeds through a well-organized transition state, thereby affording products with up to 94% ee and a broad scope. The process is found to be scalable. The initial mechanistic study supports the bifunctional nature of the newly designed NHC.

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Openalex Percentile: Top 69%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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BifunctionalNHC-Catalyzed Asymmetric IntramolecularConjugate Addition via Noncovalent Interaction · Figshare (2025) | TGRS Research Map | TGRS