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Synthesis of chiral benzene-based tetraoxazolines and their application in asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes

Paper ID Volume ID Publish Year Pages File Format Full-Text
49677 46759 2014 4 PDF Available
Title
Synthesis of chiral benzene-based tetraoxazolines and their application in asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes
Abstract

•A series of new chiral benzene-based tetraoxazoline ligands were prepared.•The catalytic system is composed of the synthesized tetraoxazoline and ZnCl2.•The catalytic system was tested in asymmetric Friedel–Crafts alkylations.•The catalytic system presented excellent activities and enantioselectivities.

A series of new chiral benzene-based tetraoxazoline ligands were prepared in good yields through the reaction of 1,2,4,5-benzenetetracarboxylic acid and chiral β-amino alcohols by continuous removal of water, and the asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes was tested using the chiral catalysts, which were generated in situ by refluxing the above ligands and anhydrous zinc chloride in solvent. In most case, good yields (up to 99%) and excellent enantioselectivities (up to 98% ee) were obtained.

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Keywords
Tetraoxazoline; Asymmetric catalysis; Friedel–Crafts alkylation; Indole derivative; Nitroalkene
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Synthesis of chiral benzene-based tetraoxazolines and their application in asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 52, 5 July 2014, Pages 53–56
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us