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Query: faculty: "FNWI" and publication year: "2008"

AuthorsN.V. Sewgobind, M.J. Wanner, S. Ingemann, R. de Gelder, J.H. van Maarseveen, H. Hiemstra
TitleEnantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine
JournalJournal of Organic Chemistry
Volume73
Year2008
Issue16
Pages6405-6408
ISSN00223263
FacultyFaculty of Science
Institute/dept.FNWI: Van 't Hoff Institute for Molecular Sciences (HIMS)
AbstractOptically active tetrahydro-beta-carbolines were synthesized via an (R)-BINOL-phosphoric acid-catalyzed asynunetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic and aliphatic aldehydes. The tetrahydro-beta-carbolines were obtained in yields ranging from 77% to 97% and with ee values up to 87%. The triphenylsilyl-substituted BINOL-phosphoric acid proved to be the catalyst of choice for the reaction with aromatic aldehydes. For the aliphatic aldehydes, 3,5 -bistrifluoromethylphenyL-substituted BINOL-phosphoric acid was identified as the best catalyst.
Document typeArticle
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