ArticleChemical science2020
Chemo-selective cross reaction of two enals
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
What it found
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Who cites it
3 citing papers in PubMed.
- Computational Library Enables Pattern Recognition of Noncovalent Interactions and Application as a Modern Linear Free Energy Relationship.The Journal of organic chemistry · 2024Article
- Organocatalytic diastereo- and atroposelective construction of N-N axially chiral pyrroles and indoles.Nature communications · 2024Article
- Recent Advances in the Synthesis of 3,4-Dihydropyran-2-Ones Organocatalyzed byMolecules (Basel, Switzerland) · 2023Review
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A dual catalytic chemo-selective cross-coupling reaction of two enals is developed. One enal (without α-substitution) is activated by an NHC catalyst to form an acylazolium enolate intermediate that undergoes Michael-type addition to another enal molecule bearing an alkynyl substituent. Mechanistic studies indicate that non-covalent interactions between the alkynyl enal and the NHC·HX catalyst play important roles in substrate activation and enantioselectivity control. Many of the possible side reactions are not observed. Our reaction provides highly chemo- and diastereo-selective access to chiral lactones containing functionalizable 1,3-enyn units with excellent enantioselectivities (95 to >99% ee).
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.