Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts

[Display omitted] A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumbered tert-butyl squaramide/qu...

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Bibliographic Details
Published inTetrahedron letters Vol. 73; pp. 153153 - 153156
Main Authors Dündar, Esra, Tanyeli, Cihangir
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.06.2021
Elsevier
Subjects
Asymmetric synthesis
Chemistry
Chemistry, Organic
Friedel-Crafts alkylation
Indole
Organocatalysis
Physical Sciences
Science & Technology
Squaramide organocatalyst
Squaramide organocatalyst
Asymmetric synthesis
Friedel-Crafts alkylation
Organocatalysis
Indole
CATALYST
DERIVATIVES
MICHAEL ADDITION
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Summary:[Display omitted] A series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumbered tert-butyl squaramide/quinine with high enantioselectivity (up to >99% ee) and moderate chemical yields (up to 80%) by representing as chiral precursors for very important biologically active molecules. Besides, this asymmetric transformation provides a very simple, efficient, clean and environmental friendly route. In addition, this process has very mild reaction conditions such as ambient temperature and usage of only 2 mol% catalyst loading compared to previous studies in literature.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153153