InCl3-catalyzed asymmetric aza-Friedel–Crafts reaction of indoles with imines generated from O-pivaloylated β-d-galactosylamine
- Resource Type
- Article
- Authors
- Li, Bo-Yu; Li, Zhong-Jun; Meng, Xiang-Bao
- Source
- Carbohydrate Research. Aug2010, Vol. 345 Issue 12, p1708-1712. 5p.
- Subject
- *FRIEDEL-Crafts reaction
*ASYMMETRIC synthesis
*METHANE
*INDOLE
*ASYMMETRY (Chemistry)
*METHANOL
*CARBOHYDRATES
*IMINES
- Language
- ISSN
- 0008-6215
Abstract: The highly diastereoselective InCl3-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 β-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/H2O subsequently, to yield the 3-indolyl aryl methanamine derivatives in high optical purity. [ABSTRACT FROM AUTHOR]