1040446-41-0Relevant academic research and scientific papers
The cinchona alkaloid squaramide catalyzed asymmetric Pictet-Spengler reaction and related theoretical studies
Qi, Liang,Hou, Huacui,Ling, Fei,Zhong, Weihui
, p. 566 - 574 (2018)
The asymmetric Pictet-Spengler reaction between tryptamine derivatives and aldehydes has been developed with a cinchona alkaloid squaramide as the catalyst, affording the corresponding tetrahedron-β-carbolines in good to excellent yields and ee values. A rational mechanistic pathway has also been proposed based on DFT calculations.
Enantioselective BINOL-phosphoric acid catalyzed Pictet - Spengler reactions of N-benzyltryptamine
Sewgobind, Nishant V.,Wanner, Martin J.,Ingemann, Steen,De Gelder, Rene,Van Maarseveen, Jan H.,Hiemstra, Henk
, p. 6405 - 6408 (2008/12/22)
(Chemical Equation Presented) Optically active tetrahydro-β-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-β-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.
