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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Westermaier et al. (2007) studied this question.
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