Cyclodextrin host as a supramolecular catalyst in nonpolar solvents: stereoselective synthesis of (E)-3-alkylideneoxindoles

Heptakis(6-O-triisopropylsilyl)-β-cyclodextrin (TIPS-β-CD) effectively formed inclusion complexes with oxindole and its derivatives as guests in nonpolar solvents. Their inclusion complex formation was remarkably affected by the position and size of substituents on the oxindole ring of the guest. Th...

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Bibliographic Details
Published in:Tetrahedron 2013-11, Vol.69 (45), p.9428-9433
Main Authors: Asahara, Haruyasu, Kida, Toshiyuki, Hinoue, Tomoaki, Akashi, Mitsuru
Format: Article
Language:English
Subjects:
Catalysts
Cinnamaldehyde
Condensing
Cyclodextrin
Derivatives
Inclusion complex
Inclusion complexes
Oxindole
Solvents
Stereoselective reaction
Synthesis
Tetrahedrons
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Description
Summary:Heptakis(6-O-triisopropylsilyl)-β-cyclodextrin (TIPS-β-CD) effectively formed inclusion complexes with oxindole and its derivatives as guests in nonpolar solvents. Their inclusion complex formation was remarkably affected by the position and size of substituents on the oxindole ring of the guest. The Knoevenagel condensation reaction of these oxindoles with cinnamaldehyde to give 3-alkylideneoxindoles was accelerated with enhanced E/Z selectivities in the presence of catalytic amounts of TIPS-β-CD. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.08.078