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Construction of Chiral Tetrahydro‐β‐Carbolines: Asymmetric Pictet–Spengler Reaction of Indolyl Dihydropyridines
Author(s) -
Wang ShouGuo,
Xia ZiLei,
Xu RenQi,
Liu XiJia,
Zheng Chao,
You ShuLi
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703178
Subject(s) - pictet–spengler reaction , phosphoric acid , chemistry , reaction conditions , combinatorial chemistry , catalysis , organic chemistry
A highly efficient synthesis of the enantioenriched tetrahydro‐β‐carbolines was developed by using a chiral phosphoric acid catalyzed Pictet–Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro‐β‐carbolines in good to excellent yields (up to 96 %) and high enantioselectivities (up to 99 % ee ). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner.