Query:
faculty: "FNWI" and publication year: "2008"
| Authors | N.V. Sewgobind, M.J. Wanner, S. Ingemann, R. de Gelder, J.H. van Maarseveen, H. Hiemstra | | Title | Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine |
| Journal | Journal of Organic Chemistry |
| Volume | 73 |
| Year | 2008 |
| Issue | 16 |
| Pages | 6405-6408 |
| ISSN | 00223263 |
| Faculty | Faculty of Science |
| Institute/dept. | FNWI: Van 't Hoff Institute for Molecular Sciences (HIMS) |
| Abstract | Optically 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 type | Article |
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