Ruthenium-Porphyrin-Catalyzed [4+2] Cycloaddition of α,β-Unsaturated Imines and Aldehydes

被引：20

作者：

Maeda, Kazuki ^{[1
]}

Terada, Takuma ^{[1
]}

Iwamoto, Takahiro ^{[1
]}

Kurahashi, Takuya ^{[1
,2
]}

Matsubara, Seijiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan

[2] ACT C, JST, Kawaguchi, Saitama 3320012, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 21期

基金：

日本科学技术振兴机构;

关键词：

C-H BONDS; BIOMIMETIC ASYMMETRIC HYDROGENATION; IN-SITU; MANGANESE PORPHYRIN; ALKENES; 1,4-DIHYDROPYRIDINES; DIHYDROPYRIDINES; CYCLOPROPANATION; TOSYLHYDRAZONES; CONSTRUCTION;

D O I：

10.1021/acs.orglett.5b02654

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthetic route to unsymmetrically substituted dihydropyridine scaffolds via dehydrative [4+2] cycloaddition of N-tosylated alpha,beta-unsaturated imines with aldehydes has been developed. This transformation is enabled by (i) the remarkable catalytic ability of the cationic Ru(IV) porphyrin complex to activate both the imino and carbonyl groups and (ii) the hydrophobic nature of the porphyrin ligand, which helps realize robust Lewis acidity in the dehydrative cycloaddition.

引用

页码：5284 / 5287

页数：4

共 42 条

[21]

Liang JL, 2002, CHEM-EUR J, V8, P1563, DOI 10.1002/1521-3765(20020402)8:7<1563::AID-CHEM1563>3.0.CO

[22]

2-V

[23] Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin [J].

Liu, Wei ;

Huang, Xiongyi ;

Cheng, Mu-Jeng ;

Nielsen, Robert J. ;

Goddard, William A., III ;

Groves, John T. .

SCIENCE, 2012, 337 (6100) :1322-1325

[24]

LOEV B, 1974, J MED CHEM, V17, P956, DOI 10.1021/jm00255a010

[25] Tacripyrines, the First Tacrine-Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease [J].

Marco-Contelles, Jose ;

Leon, Rafael ;

de los Rios, Cristobal ;

Samadi, Abdelouahid ;

Bartolini, Manuela ;

Andrisano, Vincenza ;

Huertas, Oscar ;

Barril, Xavier ;

Javier Luque, F. ;

Rodriguez-Franco, Maria I. ;

Lopez, Beatriz ;

Lopez, Manuela G. ;

Garcia, Antonio G. ;

do Carmo Carreiras, Maria ;

Villarroya, Mercedes .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) :2724-2732

[26] Organocatalytic asymmetric transfer hydrogenation of nitroolefins [J].

Martin, Nolwenn J. A. ;

Ozores, Lidia ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :8976-+

[27] A Reaction of Triazoles with Thioesters to Produce β-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond [J].

Miura, Tomoya ;

Fujimoto, Yoshikazu ;

Funakoshi, Yuuta ;

Murakami, Masahiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9967-9970

[28] Iron-Catalyzed Cyclopropanation in 6 M KOH with in Situ Generation of Diazomethane [J].

Morandi, Bill ;

Carreira, Erick M. .

SCIENCE, 2012, 335 (6075) :1471-1474

[29] Enantioselective Organocatalytic Aza-Ene-Type Domino Reaction Leading to 1,4-Dihydropyridines [J].

Noole, Artur ;

Borissova, Maria ;

Lopp, Margus ;

Kanger, Tonis .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) :1538-1545

[30] Enantioselective organocatalytic hydride reduction [J].

Ouellet, SG ;

Tuttle, JB ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :32-33

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