title: Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles.
abstract: A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and pyrroles and the subsequent Pd-catalyzed hydrogenolysis of the methylbenzyl group provided the products in high yields and excellent enantioselectivities.
authors.affiliation: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, Massachusetts 02125-3393, USA.
authors.forename: Mohammed
authors.initials: M
authors.lastname: Abid
authors.forename: Liliana
authors.initials: L
authors.lastname: Teixeira
authors.forename: Béla
authors.initials: B
authors.lastname: Török
mesh_terms: D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D008698:Mesylates; D011758:Pyrroles; C012077:trifluoromethanesulfonic acid; D005998:Glycine