- Synthesis of enantiopure (S)-indolylglycine by organocatalyzed Friedel-Crafts alkylation of indole
- European Journal of Organic Chemistry
- Volume | Issue number
- Pages (from-to)
- Document type
- Faculty of Science (FNWI)
- Van 't Hoff Institute for Molecular Sciences (HIMS)
Tritylsulfenyl- and 2-nitrophenylsulfenyl-substituted glyoxyl imines were used in chiral phosphoric acid catalyzed Friedel-Crafts (FC) reactions with indole. High yields and ee values ranging from 86% for Nps-protected (S)-indolylglycine to 88% for Trs-protected (R)-indolylglycine were obtained. On a preparative scale, a FC product with 99.5% ee and 71% yield was readily obtained by crystallization of the reaction mixture. Removal of the Nps protecting group under mild acidic conditions did not affect the stereochemical integrity of the alpha-carbon atom and (S)-indolylglycine was afforded in >= 98% ee.
- go to publisher's site
If you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library, or send a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible.