title: A Brønsted acid catalyst for the enantioselective protonation reaction.
abstract: A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity.
authors.affiliation: Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Cheol Hong
authors.initials: CH
authors.lastname: Cheon
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D063088:Phosphoramides; D010756:Phosphoric Acids / Q000737:chemistry*; D011522:Protons; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D004987:Ethers; D063088:Phosphoramides; D010756:Phosphoric Acids; D011522:Protons; D012821:Silanes; D013438:Sulfhydryl Compounds; C005438:phosphoramide