Bronsted Acid-Thiourea Co-catalysis: Asymmetric Synthesis of Functionalized 1,4-Dihydropyridines from β-Enamino Esters and α,β-Unsaturated Aldehydes

被引：24

作者：

Yoshida, Kohzo ^{[1
]}

Inokuma, Tsubasa ^{[1
]}

Takasu, Kiyosei ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

SYNLETT | 2010年 / 12期

关键词：

asymmetric organocatalysis; Bronsted acid; thiourea; 1,4-dihydropyridines; beta-enamino esters; alpha; beta-unsaturated aldehydes; 3-COMPONENT DOMINO SYNTHESIS; SOLVENT-FREE CONDITIONS; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; ALPHA-ACYLOXYACROLEINS; EFFICIENT SYNTHESIS; BIGINELLI REACTION; MICHAEL REACTION; DIHYDROPYRIMIDINONES; ACTIVATION;

D O I：

10.1055/s-0030-1258090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Bronsted acid and a novel thiourea derivative co-catalyze the addition of beta-enamino esters to alpha,beta-unsaturated aldehydes leading to functionalized 1,4-dihydropyridines with moderate to good enantioselectivity. A regioselective synthesis of 1,2-dihydropyridines from alpha,beta-unsaturated aldehydes is also described.

引用

页码：1865 / 1869

页数：5

共 22 条

[1] Weak Bronsted Acid-Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet-Spengler Reactions
Klausen, Rebekka S.
Jacobsen, Eric N.
ORGANIC LETTERS, 2009, 11 (04) : 887 - 890
[2] α,β-Unsaturated Aldehydes as C-Building Blocks in the Synthesis of Pyridines, 1,4-Dihydropyridines and 1,2-Dihydropyridines
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ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1207 - 1226
[3] Rapid and Efficient Synthesis of 1,4-Dihydropyridines using a Sulfonic Acid-functionalized Ionic Liquid
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[4] EFFICIENT AND RAPID SYNTHESIS OF HIGHLY FUNCTIONALIZED NOVEL SYMMETRIC 1,4-DIHYDROPYRIDINES USING GLACIAL ACETIC ACID AS SOLVENT
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[5] Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions
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[6] Halloysite Nanotubes Functionalized Sulfonic Acid: Synthesis, Spectro-scopic Characterization, Computational Studies and Application for the Synthesis of 1,4-Dihydropyridines
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LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (01) : 19 - 27
[7] Sulfonic acid-functionalized nano zeolite NaY: a Brønsted acid catalyst for the green synthesis of pyridines and 1,4-dihydropyridines
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NEW JOURNAL OF CHEMISTRY, 2025, 49 (06) : 2418 - 2431
[8] Catalytic Asymmetric Synthesis of Both Enantiomers of 4-Substituted 1,4-Dihydropyridines with the Use of Bifunctional Thiourea-Ammonium Salts Bearing Different Counterions
Yoshida, Kohzo
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MOLECULES, 2010, 15 (11) : 8305 - 8326
[9] Sulfonic acid-functionalized silica: a remarkably efficient heterogeneous reusable catalyst for the one-pot synthesis of 1,4-dihydropyridines
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TURKISH JOURNAL OF CHEMISTRY, 2010, 34 (04) : 613 - 619
[10] Asymmetric Synthesis of 1,4-Dicarbonyl Compounds from Aldehydes by Hydrogen Atom Transfer Photocatalysis and Chiral Lewis Acid Catalysis
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Shi, Xiangcheng
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (47) : 16859 - 16863

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