Sewgobind Nishant V, Wanner Martin J, Ingemann Steen, de Gelder René, van Maarseveen Jan H, Hiemstra Henk
Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
J Org Chem. 2008 Aug 15;73(16):6405-8. doi: 10.1021/jo8010478. Epub 2008 Jul 11.
Optically active tetrahydro-beta-carbolines were synthesized via an ( R)-BINOL-phosphoric acid-catalyzed asymmetric 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.
通过（R）-联萘酚磷酸催化N-苄基色胺与一系列芳香族和脂肪族醛的不对称Pictet-Spengler反应合成了光学活性的四氢-β-咔啉。四氢-β-咔啉的产率为77%至97%，对映体过量值高达87%。三苯基硅基取代的联萘酚磷酸被证明是与芳香醛反应的首选催化剂。对于脂肪族醛，3,5-双三氟甲基苯基取代的联萘酚磷酸被确定为最佳催化剂。
