Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles.
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.
Abid
Mohammed
M
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, Massachusetts 02125-3393, USA.
Teixeira
Liliana
L
Török
Béla
B
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
D000588:Amines; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D008698:Mesylates; D011758:Pyrroles; C012077:trifluoromethanesulfonic acid; D005998:Glycine