Asymmetric Ring Opening of Oxabicyclic Alkenes: Enhanced Rhodium Catalysis Using Camphor-Derived NHC Ligands Featuring Pyridine Coordination

The synthesis, characterization, and reactivity assessment of a chiral camphor-based Rh(I) catalyst functionalized with a pyridine moiety is presented. The catalytic system was evaluated in the asymmetric ring opening (ARO) of bicyclic alkene substrates, ensuring high product yields and enantioselectivity. While the primary focus was on the use of indoles as nucleophiles in the ARO reaction, a broader scope of bicyclic substrates was also explored. The catalyst demonstrated tolerance toward various functional groups present in the nucleophiles, underscoring its broad synthetic utility in asymmetric synthesis.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-05
DOI
https://doi.org/10.1021/acs.joc.5c02582
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

Asymmetric Ring Opening of Oxabicyclic Alkenes: Enhanced Rhodium Catalysis Using Camphor-Derived NHC Ligands Featuring Pyridine Coordination

René Wilhelm, Daniel Kamzol, Wende Chen
The Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

Asymmetric Ring Opening of Oxabicyclic Alkenes: Enhanced Rhodium Catalysis Using Camphor-Derived NHC Ligands Featuring Pyridine Coordination

René Wilhelm, Daniel Kamzol, Wende Chen
article en

Abstract

The synthesis, characterization, and reactivity assessment of a chiral camphor-based Rh(I) catalyst functionalized with a pyridine moiety is presented. The catalytic system was evaluated in the asymmetric ring opening (ARO) of bicyclic alkene substrates, ensuring high product yields and enantioselectivity. While the primary focus was on the use of indoles as nucleophiles in the ARO reaction, a broader scope of bicyclic substrates was also explored. The catalyst demonstrated tolerance toward various functional groups present in the nucleophiles, underscoring its broad synthetic utility in asymmetric synthesis.

The Journal of Organic ChemistryVol. 91(9)
Clausthal University of Technology (DE)
Openalex Percentile: Top 97%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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