Enantioselective synthesis of (3-indolyl)glycine derivatives via asymmetric Friedel–Crafts reaction between indoles and glyoxylate imines

Chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts reaction of indoles with ethyl glyoxylate imines was developed. With 10 mol % of the catalyst, the Friedel–Crafts reactions between a wide range of indoles and imines have been carried out, affording optically active (3-indolyl)glycine...

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Bibliographic Details
Published in:Tetrahedron 2009-02, Vol.65 (8), p.1603-1607
Main Authors: Kang, Qiang, Zhao, Zhuo-An, You, Shu-Li
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts reaction of indoles with ethyl glyoxylate imines was developed. With 10 mol % of the catalyst, the Friedel–Crafts reactions between a wide range of indoles and imines have been carried out, affording optically active (3-indolyl)glycine derivatives with excellent yields and high enantioselectivities (up to 87% ee). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.12.061