Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones.
Chiral complexes of BINOL-based ligands with zirconium tert-butoxide catalyze the Friedel-Crafts alkylation reaction of indoles with beta-trifluoromethyl-alpha,beta-unsaturated ketones to give functionalized indoles with an asymmetric tertiary carbon center attached to a trifluoromethyl group. The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%.
Blay
Gonzalo
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 59, 46100 Burjassot, València, Spain.
Fernández
Isabel
I
Muñoz
M Carmen
MC
Pedro
José R
JR
Vila
Carlos
C
D000478:Alkylation; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D007659:Ketones; D008024:Ligands; D002244:Carbon; D015040:Zirconium