AgAsF6/Sm(OTf)3 promoted reversal of enantioselectivity for the asymmetric Friedel-Crafts alkylations of indoles with beta,gamma-unsaturated alpha-ketoesters.
The first example of central metal controlled reversal of enantioselectivity in asymmetric Friedel-Crafts alkylation of indoles and beta,gamma-unsaturated alpha-ketoesters has been developed. Using the same chiral starting material derived N,N'-dioxides 1a and 1b as ligands, various indole esters 4 were obtained in good to excellent yields and enantioselectivities. The reaction also featured mild reaction conditions and remarkably low catalyst loading (down to 0.01 mol %).
Liu
Yanling
Y
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Shang
Deju
D
Zhou
Xin
X
Zhu
Yin
Y
Lin
Lili
L
Liu
Xiaohua
X
Feng
Xiaoming
X
D000478:Alkylation; D002384:Catalysis; D004952:Esters; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004952:Esters; D007211:Indoles; D007659:Ketones; D008670:Metals