Synthesis of Enantiopure (S)??Indolylglycine by Organocatalyzed Friedel–Crafts Alkylation of Indole
MJ Wanner, P Hauwert, HE Schoemaker…
Index: Wanner, Martin J.; Hauwert, Peter; Schoemaker, Hans E.; De Gelder, Rene; Van Maarseveen, Jan H.; Hiemstra, Henk European Journal of Organic Chemistry, 2008 , # 1 p. 180 - 185
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Citation Number: 32
Abstract
Abstract Tritylsulfenyl-and 2-nitrophenylsulfenyl-substituted glyoxyl imines were used in chiral phosphoric acid catalyzedFriedel–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 ...
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