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

[21] An efficient Mannich-type one-pot synthesis of 3,5,7,11-tetraazatricyclo [7.3.1.02,7]tridec-2-ene derivatives starting from functionalized 1,4-dihydropyridines
Dotsenko, Victor V.
Krivokolysko, Sergey G.
Chernega, Alexander N.
Litvinov, Victor P.
MONATSHEFTE FUR CHEMIE, 2007, 138 (01): : 35 - 42
[22] An Efficient Mannich-Type One-Pot Synthesis of 3,5,7,11-Tetraazatricyclo [7.3.1.02,7]tridec-2-ene Derivatives Starting from Functionalized 1,4-Dihydropyridines
Victor V. Dotsenko
Sergey G. Krivokolysko
Alexander N. Chernega
Victor P. Litvinov
Monatshefte für Chemie - Chemical Monthly, 2007, 138 : 35 - 42

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