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

Date

2021-01-01

Author

Dündar, Esra
Tanyeli, Cihangir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

204
views

0
downloads

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.

URI

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

Suggestions

OpenMETU
Core

Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides KANBEROĞLU, Esra; Tanyeli, Cihangir (2016-01-01) A family of chiral bifunctional acid-/base-type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1-nitropropane to various trans--nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 degrees C by using a catalyst loading of only 2mol% to afford the 1,3-dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95%ee and syn/anti isomers ...
Enantioselective Michael Addition of Nitroalkanes to Nitroalkenes Catalyzed by Chiral Bifunctional Quinine-Based Squaramides Kanberoğlu, Esra; Tanyeli, Cihangir (Wiley, 2015-10-26) A family of chiral bifunctional acid-/base-type quinine/squaramide organocatalysts is shown to be highly active promoters of the conjugate addition of 1-nitropropane to various trans-β-nitroalkenes. The cooperation of the quinine and the sterically encumbered squaramide moieties catalyzed the Michael addition reactions at 0 °C by using a catalyst loading of only 2 mol % to afford the 1,3-dinitro Michael adducts with excellent enantioselectivity and diastereoselectivity (up to 95 % ee and syn/anti isomers
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01) New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Enantioselective reduction of ketones with borane catalyzed by cyclic β- amino alcohols prepared from proline Demir, Ayhan S; Mecitoglu, Idris; Tanyeli, Cihangir; Gülbeyaz, Volkan (Elsevier BV, 1996-12) New catalysts have been prepared from (S)- and (R)- proline and the asymmetric borane reduction of prochiral ketones using these catalysts has been studied. The secondary alcohols were obtained in 76-95% yield with 57-96% enantiomeric excesses. Copyright (C) 1996 Elsevier Science Ltd
Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods Demir, Ayhan Sıtkı; Caliskan, Zerrin; Sahin, Ertan (Elsevier BV, 2007-03-01) The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acet...

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.