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
收藏
页码：3381 / 3387
页数：7
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