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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.

ABSTRACT: Five new C2-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.

SUBMITTER: Islam MS 

PROVIDER: S-EPMC8658940 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Exploiting the Chiral Ligands of <i>Bis</i>(imidazolinyl)- and <i>Bis</i>(oxazolinyl)thiophenes-Synthesis and Application in Cu-Catalyzed Friedel-Crafts Asymmetric Alkylation.

Islam Mohammad Shahidul MS   Alammari Abdullah Saleh AS   Barakat Assem A   Alshahrani Saeed S   Haukka Matti M   Al-Majid Abdullah Mohammed AM  

Molecules (Basel, Switzerland) 20211206 23

Five new <i>C</i><sub>2</sub>-symmetric chiral ligands of 2,5-<i>bis</i>(imidazolinyl)thiophene (<b>L1</b><b>-L3</b>) and 2,5-<i>bis</i>(oxazolinyl)thiophene (<b>L4</b> and <b>L5</b>) were synthesized from thiophene-2,5-dicarboxylic acid (<b>1</b>) with enantiopure amino alcohols (<b>4a</b>-<b>c</b>) 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 <b>L5</b>  ...[more]

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