title: Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 moiety.
abstract: A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.
authors.forename: Ralph
authors.initials: R
authors.lastname: Husmann
authors.forename: Erli
authors.initials: E
authors.lastname: Sugiono
authors.forename: Stefanie
authors.initials: S
authors.lastname: Mersmann
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010755:Organophosphates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D010755:Organophosphates