We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Diastereoselective Formation of Quaternary Stereocenters in Imidazole N -Oxide Cycloaddition with Fluoroalkenes.
- Authors
Bukowska, Patrycja; Loska, Rafał
- Abstract
Imidazole N-oxides are attractive starting materials for the preparation of complex molecules containing an imidazole ring. Dipolar cycloaddition between 1,1-difluoroalkenes and imidazole N-oxides bearing a chiral auxiliary performed in the presence of oxygen or nitrogen nucleophiles was found to provide access to esters and amides bearing a 2-azaheteroaryl substituent at the α position of the imidazole ring as mixtures of diastereomers that, in most cases, are readily separable. This three-component reaction introduces a new tertiary or quaternary all-carbon stereocenter into the heterocyclic ring at a position originally occupied by hydrogen. Importantly, products containing a trifluoromethyl group attached to this stereocenter are readily available as well.
- Subjects
DIASTEREOISOMERS; NUCLEOPHILES; AMIDES; ESTERS; RING formation (Chemistry); NITRILE oxides; HYDROGEN; IMIDAZOLES
- Publication
Catalysts (2073-4344), 2022, Vol 12, Issue 2, p177
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal12020177