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Zoekopdracht: faculteit: "FNWI" en publicatiejaar: "2008"

AuteursM.J. Wanner, P. Hauwert, H.E. Schoemaker, R. de Gelder, J.H. van Maarseveen, H. Hiemstra
TitelSynthesis of enantiopure (S)-indolylglycine by organocatalyzed Friedel-Crafts alkylation of indole
TijdschriftEuropean Journal of Organic Chemistry
Jaar2008
Nummer1
Pagina's180-185
ISSN1434193X
FaculteitFaculteit der Natuurwetenschappen, Wiskunde en Informatica
Instituut/afd.FNWI: Van 't Hoff Institute for Molecular Sciences (HIMS)
SamenvattingTritylsulfenyl- 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.
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