ArticleNature communications2022
Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Review
- Stereoselective diversification of α-amino acids enabled by N-heterocyclic carbene catalysis.Nature communications · 2025Article
- An analysis method including orbital overlap directions for predicting π electron properties and reactivity vectors.Nature communications · 2025Article
- Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent.Nature communications · 2024Article
- Amide C-N bonds activation by A new variant of bifunctional N-heterocyclic carbene.Nature communications · 2024Article
- Recent advances in catalytic asymmetric synthesis.Frontiers in chemistry · 2024Review
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Authors and funding
13 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Over the past decade, the catalysis of N-heterocyclic carbenes has achieved significant advances. In this area, aldehydes, enals, and esters, are commonly employed as starting materials through various catalytic activation modes. However, NHC-activated strategy of amide and its derivatives remains elusive. Described herein is the realization of asymmetric desymmetrization of N-Cbz glutarimides with alcohols through an imide C-N bond cleavage under NHC organocatalysis. A structurally diverse set of enantioenriched 4-amido esters is generated with acceptable yields and high enantioselectivities. This method features mild reaction conditions, excellent substrate scope, and excellent atom economy. DFT calculations have been performed to explore the detailed reaction mechanism and the origin of the enantioselectivity, which indicate that the strength of the C-H···O hydrogen bond and C-H⋯π interactions should be responsible for the stereoselectivity. The current strategy could open a door for efficient construction of (R)-Rolipram with excellent stereoselectivity.
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Registered trials
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