InCl(3)-catalyzed asymmetric aza-Friedel-Crafts reaction of indoles with imines generated from O-pivaloylated beta-D-galactosylamine.
The highly diastereoselective InCl(3)-catalyzed aza-Friedel-Crafts reaction of substituted indoles with aldimines generated from Kunz's amine was studied. The reaction afforded the desired product in good to high yields with up to >19:1 diastereoselective ratios. The O-pivaloylated beta-D-galactosyl moiety could not be cleaved under the traditional acidic conditions. It was removed successfully after unmasking of the O-pivaloyl groups using MeOH/NaOMe and treatment with HOAc/H(2)O subsequently, to yield the 3-indolyl aryl methanamine derivatives in high optical purity.
Li
Bo-Yu
BY
State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
Li
Zhong-Jun
ZJ
Meng
Xiang-Bao
XB
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D005688:Galactosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008744:Methylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001372:Aza Compounds; D007097:Imines; D007211:Indoles; D008744:Methylamines; D007204:Indium; C020758:indium trichloride; D005688:Galactosamine; C027451:methylamine