Mechanism and conditions for highly enantioselective epoxidation of alpha,beta-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt.
[formula: see text] Highly enantioselective (up to 130:1) epoxidation of a variety of alpha,beta-enones to form alpha,beta-epoxy ketones is described along with a rational analysis of the mechanistic basis for this strong absolute stereochemical control by the chiral catalyst 2.
Corey
E J
EJ
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. corey@chemistry.harvard.edu
Zhang
F Y
FY
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007659:Ketones; D000644:Quaternary Ammonium Compounds; D012492:Salts