Fe-Catalyzed Allylic C-C-Bond Activation: Vinylcyclopropanes As Versatile a1,a3,d5-Synthons in Traceless Allylic Substitutions and [3+2]-Cycloadditions

被引：159

作者：

Dieskau, Andre P. ^{[1
]}

Holzwarth, Michael S. ^{[1
]}

Plietker, Bernd ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, DE-70569 Stuttgart, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 11期

关键词：

CARBON-CARBON BOND; DONOR-ACCEPTOR CYCLOPROPANES; VINYL AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; ALLYLBORONIC ACIDS; 3+2 CYCLOADDITION; RING-CLEAVAGE; ACCESS; COMPLEXES; CYCLOHEXENONES;

D O I：

10.1021/ja300294a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The low-valent iron complex Bu4N[Fe-(CO)(3)(NO)] (TBAFe) catalyzes the allylic C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.

引用

页码：5048 / 5051

页数：4

共 67 条

[1] Selective, catalytic carbon-carbon bond activation and functionalization promoted by late transition metal catalysts [J].

Bart, SC ;

Chirik, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :886-887

[2] An Efficient Iron-Catalyzed Carbon-Carbon Single-Bond Cleavage via Retro-Claisen Condensation: A Mild and Convenient Approach to Synthesize a Variety of Esters or Ketones [J].

Biswas, Srijit ;

Maiti, Sukhendu ;

Jana, Umasish .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (15) :2861-2866

[3] Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans [J].

Bowman, RK ;

Johnson, JS .

ORGANIC LETTERS, 2006, 8 (04) :573-576

[4] REGIOSELECTIVE AND STEREOSELECTIVE NUCLEOPHILIC-ADDITION TO ELECTROPHILIC VINYLCYCLOPROPANES [J].

BURGESS, K .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :2046-2051

[5] Reaction of vinyl epoxides with palladium-switchable bisnucleophiles:: Synthesis of carbocycles [J].

Castaño, AM ;

Méndez, M ;

Ruano, M ;

Echavarren, AM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :589-593

[6] Combined Rhodium-Catalyzed Carbon-Hydrogen Activation and β-Carbon Elimination to access Eight-Membered Rings [J].

Crepin, Damien ;

Dawick, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (03) :620-623

[7] Bu4N[Fe(CO)3(NO)]-Catalyzed Hydrosilylation of Aldehydes and Ketones [J].

Dieskau, Andre P. ;

Begouin, Jeanne-Marie ;

Plietker, Bernd .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) :5291-5296

[8] A Mild Ligand-Free Iron-Catalyzed Liberation of Alcohols from Allylcarbonates [J].

Dieskau, Andre P. ;

Plietker, Bernd .

ORGANIC LETTERS, 2011, 13 (20) :5544-5547

[9] Catalytic Carbon-Carbon σ Bond Activation: An Intramolecular Carbo-Acylation Reaction with Acylquinolines [J].

Dreis, Ashley M. ;

Douglas, Christopher J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :412-+

[10]

EISENSTADT A, 1972, TETRAHEDRON LETT, P2005

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