4.6 Article

Chiral phosphoric acid-catalyzed Friedel-Crafts reaction of 2,5-disubstituted and 2-monosubstituted pyrroles with isoindolinone-derived ketimines

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 21, 期 16, 页码 3381-3387

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob00326d

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This paper describes the enantioselective reaction between 2,5-disubstituted pyrroles and diaryl-ketimines generated from isoindolinone-derived alcohols. Pyrrole derivatives with a congested tetrasubstituted stereogenic center at the beta-(C3) position are obtained in high yields and enantioselectivities. The reaction can also be extended to 2-monosubstituted pyrroles, producing chiral alpha-(C5) functionalized pyrrole products. Control experiments were conducted to explain the origin of low enantioselectivities in some products.
The enantioselective reaction between 2,5-disubstituted pyrroles and diaryl-ketimines, generated in situ from isoindolinone-derived alcohols, is described. Pyrrole derivatives possessing a congested tetrasubstituted stereogenic center at the beta-(C3) position are generally obtained in high yields and enantioselectivities. The transformation can be extended to 2-monosubstituted pyrroles, generating chiral alpha-(C5) functionalized pyrrole products. Control experiments were conducted in order to elucidate the origin of the low enantioselectivities observed in some of the products.

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