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Regio‐ and Stereoselective Ring‐Opening Reactions of Epoxides with Indoles and Pyrroles in 2,2,2‐Trifluoroethanol
Author(s) -
Westermaier Martin,
Mayr Herbert
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701366
Subject(s) - stereoselectivity , chemistry , ring (chemistry) , epoxide , enantiomer , regioselectivity , catalysis , pyrrole , enantiomeric excess , organic chemistry , stereochemistry , enantioselective synthesis
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).