Regio- and stereoselective ring-opening reactions of epoxides with indoles and pyrroles in 2,2,2-trifluoroethanol.
Aliphatic and aromatic epoxides react regio- and stereoselectively with indoles and pyrroles in 2,2,2-trifluoroethanol without the use of a catalyst or any other additive. While aromatic epoxides are selectively attacked at the benzylic position, aliphatic epoxides react at the less-substituted position. Chiral epoxides react with >99 % ee (ee=enantiomeric excess).
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377 Munich, Germany.
Martin
M
Westermaier
Herbert
H
Mayr
D001554:Benzene / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004852:Epoxy Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008956:Models, Chemical; D011758:Pyrroles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D014270:Trifluoroethanol / Q000737:chemistry*
D004852:Epoxy Compounds; D007211:Indoles; D011758:Pyrroles; D012997:Solvents; D014270:Trifluoroethanol; D001554:Benzene