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Enantioselective Friedel–Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed by N,N′ ‐Dioxide–Scandium(III) Complexes: Asymmetric Synthesis of β ‐Carbolines
Author(s) -
Liu Yanling,
Shang Deju,
Zhou Xin,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802210
Subject(s) - friedel–crafts reaction , scandium , enantioselective synthesis , chemistry , catalysis , tryptamines , alkylation , indole test , medicinal chemistry , organic chemistry , biochemistry , tryptamine
An efficient catalytic asymmetric Friedel–Crafts alkylation of indoles with alkylidene malonates has been developed by using a chiral N,N′ ‐dioxide–Sc(OTf) 3 complex as the catalyst (see scheme). Some optically active intermediates containing the indole skeleton have been synthesized, such as indolepropionic acid, tryptamines, and β ‐carbolines. The coordination between the scandium atom and the chiral N,N′ ‐dioxide compound has been revealed by X‐ray structure analysis.