Premium
Highly Enantioselective Zinc‐Catalyzed Friedel–Crafts Alkylation of Indoles with Ethyl Trifluoropyruvate
Author(s) -
Hui Yonghai,
Chen Weiliang,
Wang Wentao,
Jiang Jun,
Cai Yunfei,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000643
Subject(s) - enantioselective synthesis , chemistry , friedel–crafts reaction , alkylation , enantiomer , catalysis , zinc , yield (engineering) , enantiomeric excess , adduct , organic chemistry , asymmetric induction , medicinal chemistry , materials science , metallurgy
A highly enantioselective Friedel–Crafts alkylation of indoles with ethyl trifluoropyruvate has been developed using N,N′ ‐dioxide‐zinc(II) complexes. Both enantiomers of the desired adducts were obtained by the use of enantiomeric ligands in excellent results (up to 99% yield and 98% ee ) within 0.5 h under mild conditions. On the basis of the experimental results, a proposed working model was proposed to explain the origin of the asymmetric induction.