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Stereoselective Synthesis of 5-Substituted Pyrrolo[1,2-c]imidazol-3-ones: Access to Annulated Chiral Imidazol(in)ium Salts
- Source :
- Organic Letters. 12:76-79
- Publication Year :
- 2009
- Publisher :
- American Chemical Society (ACS), 2009.
-
Abstract
- A two-step synthesis of N-heterocyclic carbene (NHC) precatalysts by diastereoselective or enantioselective lithiation of pyrrolo[1,2-c]imidazol-3-ones followed by POCl(3)-induced salt formation is described. The resulting 3-chloro-pyrroloimidazol(in)ium salts may be coordinated to palladium(II) upon NHC generation with t-BuLi at low temperature. The method may facilitate exploitation of these compounds as chiral organocatalysts or ligands in metal catalysis.
- Subjects :
- Molecular Structure
Organic Chemistry
Imidazoles
Enantioselective synthesis
chemistry.chemical_element
Stereoisomerism
Biochemistry
Medicinal chemistry
Catalysis
Metal
chemistry.chemical_compound
chemistry
visual_art
visual_art.visual_art_medium
Pyrroles
Salts
Stereoselectivity
Physical and Theoretical Chemistry
Carbene
Salt formation
Palladium
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....6fa6ebfee917183bcc991df33f9213ab