Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents.
A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Lehr
Konrad
K
Michaelis
David J
DJ
Xu
Jiayi
J
Buckl
Andreas K
AK
D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D002264:Carboxylic Acids; D007093:Imidazoles; D007659:Ketones; D010165:Palladium