1040446-38-5Relevant academic research and scientific papers
Highly enantioselective pictet-spengler reaction catalyzed by SPINOL-phosphoric acids
Huang, Dan,Xu, Fangxi,Lin, Xufeng,Wang, Yanguang
supporting information; experimental part, p. 3148 - 3152 (2012/04/17)
Chiral SPINOL-phosphoric acids are highly enantioselective catalysts for the asymmetric Pictet-Spengler reaction of Nb-α-naphthylmethyl tryptamines with a series of aliphatic and aromatic aldehydes, affording optically active tetrahydro-β-carbolines in excellent yields and ee values. The current protocol has been applied in the asymmetric total synthesis of (-)-harmicine. Copyright
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.
