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

被引：3

作者：

Berisa, Arben ^{[1
]}

Gredicak, Matija ^{[1
]}

机构：

[1] Rudjer Boskovic Inst, Div Organ Chem & Biochem, Bijenicka C 54, Zagreb 10000, Croatia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 16期

关键词：

INDOLES; FUNCTIONALIZATION; ALKYLATIONS; REDUCTION;

D O I：

10.1039/d3ob00326d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3381 / 3387

页数：7