Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines
Over the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-08-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/10/9/971 |
| _version_ | 1797555452070854656 |
|---|---|
| author | Aleksandra Buchcic Anna Zawisza Stanisław Leśniak Michał Rachwalski |
| author_facet | Aleksandra Buchcic Anna Zawisza Stanisław Leśniak Michał Rachwalski |
| author_sort | Aleksandra Buchcic |
| collection | DOAJ |
| description | Over the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of a copper(I) trifluoromethanesulfonate benzene complex. The corresponding Friedel–Crafts products were achieved efficiently in terms of chemical yield and enantioselectivity (up to 85% in some cases). |
| first_indexed | 2024-03-10T16:48:40Z |
| format | Article |
| id | doaj.art-500984303c994a84814144d7172642c2 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T16:48:40Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-500984303c994a84814144d7172642c22023-11-20T11:25:13ZengMDPI AGCatalysts2073-43442020-08-0110997110.3390/catal10090971Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-PhosphinesAleksandra Buchcic0Anna Zawisza1Stanisław Leśniak2Michał Rachwalski3Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, PolandDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, PolandDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, PolandDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, PolandOver the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of a copper(I) trifluoromethanesulfonate benzene complex. The corresponding Friedel–Crafts products were achieved efficiently in terms of chemical yield and enantioselectivity (up to 85% in some cases).https://www.mdpi.com/2073-4344/10/9/971asymmetric transformationschiral aziridinyl-phosphinesenantioselective Friedel–Crafts alkylationstereoselectivity |
| spellingShingle | Aleksandra Buchcic Anna Zawisza Stanisław Leśniak Michał Rachwalski Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines Catalysts asymmetric transformations chiral aziridinyl-phosphines enantioselective Friedel–Crafts alkylation stereoselectivity |
| title | Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines |
| title_full | Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines |
| title_fullStr | Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines |
| title_full_unstemmed | Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines |
| title_short | Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines |
| title_sort | asymmetric friedel crafts alkylation of indoles catalyzed by chiral aziridine phosphines |
| topic | asymmetric transformations chiral aziridinyl-phosphines enantioselective Friedel–Crafts alkylation stereoselectivity |
| url | https://www.mdpi.com/2073-4344/10/9/971 |
| work_keys_str_mv | AT aleksandrabuchcic asymmetricfriedelcraftsalkylationofindolescatalyzedbychiralaziridinephosphines AT annazawisza asymmetricfriedelcraftsalkylationofindolescatalyzedbychiralaziridinephosphines AT stanisławlesniak asymmetricfriedelcraftsalkylationofindolescatalyzedbychiralaziridinephosphines AT michałrachwalski asymmetricfriedelcraftsalkylationofindolescatalyzedbychiralaziridinephosphines |