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Chiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α‐Aryl Enamides: Construction of Quaternary Carbon Atoms
Author(s) -
Jia YiXia,
Zhong Jun,
Zhu ShouFei,
Zhang CanMing,
Zhou QiLin
Publication year - 2007
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.200701067
Subject(s) - friedel–crafts reaction , indole test , brønsted–lowry acid–base theory , aryl , enantioselective synthesis , catalysis , chemistry , carbon fibers , molecule , quaternary carbon , asymmetric carbon , organic chemistry , combinatorial chemistry , medicinal chemistry , materials science , optically active , alkyl , composite number , composite material
S express : Quaternary carbon atoms are constructed in excellent yields with high enantioselectivities by a highly efficient chiral Brønsted acid catalyzed Friedel–Crafts reaction of indoles and α‐aryl enamides (see scheme). The presence of H atoms on the N atoms of both the indole and enamide moieties is essential for the reaction to occur. The indole molecule attacks from the Re face to give S ‐configured products.