Highly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives | Zendy

Kang Qiang | Zendy; Zheng XiaoJian | Zendy; You ShuLi | Zendy

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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.

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