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

Date

2021-01-01

Author

Dündar, Esra
Tanyeli, Cihangir

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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.

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https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85106329057&origin=inward
https://hdl.handle.net/11511/90884

Journal

Tetrahedron Letters

DOI

https://doi.org/10.1016/j.tetlet.2021.153153

Collections

Department of Chemistry, Article

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Citation Formats

E. Dündar and C. Tanyeli, “Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts,” Tetrahedron Letters, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85106329057&origin=inward.