Enantioselective Friedel-Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline-Zn(OTf)2 complexes

Sheng Jian Jia, Da Ming Du*

*Corresponding author for this work

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Abstract

Enantioselective Friedel-Crafts alkylation reactions of indoles with β,γ-unsaturated α-ketoesters catalyzed by novel chiral C 2-symmetric squaramide-linked bisoxazoline-Zn(OTf)2 complexes were investigated. The corresponding indole ketoesters were obtained in good to excellent yields (up to 98%) and with high enantioselectivities (up to 94% ee). This is the first report on the use of chiral squaramide-linked bisoxazoline SQBOX in a catalytic enanitioselective Friedel-Crafts alkylation reaction.

Original languageEnglish
Pages (from-to)980-988
Number of pages9
JournalTetrahedron Asymmetry
Volume25
Issue number13-14
DOIs
Publication statusPublished - 31 Jul 2014

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Jia, S. J., & Du, D. M. (2014). Enantioselective Friedel-Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline-Zn(OTf)2 complexes. Tetrahedron Asymmetry, 25(13-14), 980-988. https://doi.org/10.1016/j.tetasy.2014.05.011