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Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives
Author(s) -
Kang Qiang,
Zheng XiaoJian,
You ShuLi
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.200800263
Subject(s) - friedel–crafts reaction , enantioselective synthesis , phosphoric acid , chemistry , catalysis , benzoquinone , organocatalysis , alkylation , organic chemistry , combinatorial chemistry
Position altered! 2‐(4,7‐Dihydroindolyl) methanamine derivatives (up to >99 % ee ) are synthesized by a chiral phosphoric acid catalyzed enantioselective Friedel–Crafts reaction of 4,7‐dihydroindoles with imines. A one‐pot procedure including the asymmetric Friedel–Crafts alkylation and an oxidation of products with p ‐benzoquinone leads to 2‐indolyl methanamine derivatives in excellent ee values.