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Exploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes—Synthesis and Application in Cu-Catalyzed Friedel–Crafts Asymmetric Alkylation
| Content Provider | MDPI |
|---|---|
| Author | Islam, Mohammad Shahidul Alammari, Abdullah Saleh Barakat, Assem Alshahrani, Saeed Haukka, Matti Al-Majid, Abdullah Mohammed |
| Copyright Year | 2021 |
| Description | Five new $C_{2}$-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1 –L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The utility of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subsequently, the optimized tridentate ligand L5 and $Cu(OTf)_{2}$ catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation. |
| Starting Page | 7408 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26237408 |
| Journal | Molecules |
| Issue Number | 23 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-12-06 |
| Access Restriction | Open |
| Subject Keyword | Molecules Bis-oxazoline Bis-imidazoline Thiophene Indoles Β-nitroolefins Asymmetric Catalysis Friedel−crafts Alkylation |
| Content Type | Text |
| Resource Type | Article |
