Diastereo- and Enantioselective Synthesis of Highly Functionalized Tetrahydropyridines by Recyclable Novel Bifunctional C2-Symmetric Ionic Liquid-Supported (S)-Proline Organocatalyst

被引：4

作者：

Davanagere, Prabhakara Madivalappa ^{[1
]}

De, Mrinmoy ^{[2
]}

Chanda, Kaushik ^{[1
]}

Maiti, Barnali ^{[1
]}

机构：

[1] Vellore Inst Technol, Sch Adv Sci, Dept Chem, Vellore 632014, India

[2] Indian Inst Sci, Dept Organ Chem, Bengaluru 560012, India

来源：

CATALYSTS | 2023年 / 13卷 / 01期

关键词：

asymmetric catalysis; multicomponent reactions; stereoselectivities; functionalized tetrahydropyridines; ONE-POT SYNTHESIS; MORITA-BAYLIS-HILLMAN; MULTICOMPONENT REACTIONS; EFFICIENT; 5-COMPONENT; PROLINE; FACILE; ATOM; SOLVENTS; CATALYST;

D O I：

10.3390/catal13010209

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient, novel bifunctional C-2-symmetric ionic liquid-supported (S)-proline organocatalyst 7 was developed for a one-pot, five-component reaction involving beta-keto esters 8, aryl aldehydes 9, and aryl amines 10, affording highly functionalized tetrahydropyridines 11a-o by simultaneous generation of fives bonds and two stereogenic centers with extraordinary diastereo- and enantioselectivities (up to >99:1 dr, 95:5 er) in isopropanol with high yields (up to 92%). This protocol provides quick access to diverse enantio-enriched, highly functionalized diastereo- and enantioselective tetrahydropyridines in a green medium without any column chromatographic purification. The catalyst was recycled five times without significant loss of its catalytic activity.

引用

页数：16