Enantioselective Friedel-Crafts alkylations of alpha,beta-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.
An enantioselective Friedel-Crafts alkylation with alpha,beta-unsaturated 2-acyl imidazoles and electron-rich aromatic nucleophiles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes has been accomplished. These alpha,beta-unsaturated 2-acyl imidazoles are effective electrophiles for the Friedel-Crafts reaction. The resulting adduct 2-acyl imidazole is easily converted to amides, esters, carboxylic acids, ketones, and aldehydes by methylation and subsequent displacement of the imidazole residue.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Fandrick
Keith R
KR
Song
Hyun-Ji
HJ
D000478:Alkylation; D002384:Catalysis; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D007093:Imidazoles; D009942:Organometallic Compounds; D011725:Pyridines; D012538:Scandium