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

doi:10.1016/j.tetasy.2014.05.011

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

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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 language	English
Pages (from-to)	980-988
Number of pages	9
Journal	Tetrahedron Asymmetry
Volume	25
Issue number	13-14
DOIs	https://doi.org/10.1016/j.tetasy.2014.05.011
Publication status	Published - 31 Jul 2014

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

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.",

author = "Jia, \{Sheng Jian\} and Du, \{Da Ming\}",

year = "2014",

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doi = "10.1016/j.tetasy.2014.05.011",

language = "English",

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journal = "Tetrahedron Asymmetry",

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T1 - Enantioselective Friedel-Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline-Zn(OTf)2 complexes

AU - Jia, Sheng Jian

AU - Du, Da Ming

PY - 2014/7/31

Y1 - 2014/7/31

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84905018175

U2 - 10.1016/j.tetasy.2014.05.011

DO - 10.1016/j.tetasy.2014.05.011

M3 - Article

AN - SCOPUS:84905018175

SN - 0957-4166

VL - 25

SP - 980

EP - 988

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 13-14

ER -

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

Abstract

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