Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 5, Pages 1638-1647Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701366
Keywords
C-C coupling; electrophilic substitution; enantioselectivity; heterocycles; regioselectivity
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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).
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