Regio- and stereoselective ring-opening reactions of epoxides with indoles and pyrroles in 2,2,2-trifluoroethanol |
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| Authors: | Westermaier Martin Mayr Herbert |
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| Affiliation: | Department Chemie und Biochemie, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5–13 (Haus F), 81377 München, Germany, Fax: (+49)?89‐2180‐77717 |
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| Abstract: | 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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| Keywords: | C?C coupling electrophilic substitution enantioselectivity heterocycles regioselectivity |
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