title: Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.
abstract: The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and with enantioselectivities up to 75% at room temperature. The enantioselectivity is strongly dependent on the concentration of substrates and catalyst due to the competitive noncatalyzed reaction.
authors: Department of Chemistry, University of Massachusetts Boston, Boston, Massachusetts 02125, USA.
authors: Dmitry A
authors: DA
authors: Borkin
authors: Shainaz M
authors: SM
authors: Landge
authors: Béla
authors: B
authors: Török
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry*; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D007211:Indoles; C055298:trifluoroacetaldehyde; D000079:Acetaldehyde