Regio‐ and Stereoselective Ring‐Opening Reactions of Epoxides with Indoles and Pyrroles in 2,2,2‐Trifluoroethanol | Zendy

Westermaier Martin | Zendy; Mayr Herbert | Zendy

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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).

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