Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles

被引：38

作者：

Caille, Julien ^{[1
,2
]}

Robiette, Raphael ^{[1
]}

机构：

[1] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, Pl Louis Pasteur 1 Box L4-01-02, B-1348 Louvain La Neuve, Belgium

[2] Univ Paris Est Creteil UPEC, Inst Chim & Mat Paris Est ICMPE, UMR CNRS 7182, 2 Rue Henri Dunant, F-94320 Thiais, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 26期

关键词：

CATALYZED 5+2 CYCLOADDITIONS; DONOR-ACCEPTOR CYCLOPROPANES; INTRAMOLECULAR 3+2+2 CYCLOADDITIONS; ASYMMETRIC TOTAL-SYNTHESIS; ETHYL CYCLOPROPYLIDENEACETATE; ENE-VINYLCYCLOPROPANES; METAL; ALKYNES; ALLENES; REACTIVITY;

D O I：

10.1039/d1ob00838b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled formation of medium-sized carbocycles is a major goal in modern organic chemistry due to their widespread occurrence in natural products and pharmaceutically active ingredients. One approach consists in the use of cycloaddition reactions which notably results in high selectivities and atom-economy. To this end, cyclopropanes are ideal substrates since they can provide readily functionalized three- or five-carbon synthons. Herein we report advances made in cycloaddition reactions of cyclopropanes towards the synthesis of medium-sized carbocycles via transition metal catalysis or Lewis acid catalysis.

引用

收藏

页码：5702 / 5724

页数：23

相关论文

共 153 条

[1] Aryl vinyl cyclopropane Cope rearrangements [J].

Allegre, Kevin ;

Tunge, Jon .

TETRAHEDRON, 2019, 75 (24) :3319-3329

[2] Mechanistic Insight into the Nickel-Catalyzed Intermolecular [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate with Alkynes: DFT Calculations [J].

An, Yanhong ;

Cheng, Caihong ;

Pan, Ben ;

Wang, Zhihong .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (21) :3911-3915

[3] Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes [J].

Araya, Marisel ;

Gulias, Moises ;

Fernandez, Israel ;

Bhargava, Gaurav ;

Castedo, Luis ;

Luis Mascarenas, Jose ;

Lopez, Fernando .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (33) :10255-10259

[4] Enantioselective syntheses of tremulenediol A and tremulenolide A [J].

Ashfeld, BL ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (20) :4535-4537

[5] [Rh(CO)2Cl]2-catalyzed domino reactions involving allylic substitution and subsequent carbocyclization reactions [J].

Ashfeld, BL ;

Miller, KA ;

Smith, AJ ;

Tran, K ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (08) :1661-1663

[6] Features and applications of [Rh(CO)2Cl]2-catalyzed alkylations of unsymmetrical allylic substrates [J].

Ashfeld, Brandon L. ;

Miller, Kenneth A. ;

Smith, Anna J. ;

Tran, Kristy ;

Martin, Stephen F. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9018-9031

[7] Lewis Base Catalysis Based on Homoconjugate Addition: Rearrangement of Electron-Deficient Cyclopropanes and Their Derivatives [J].

Babu, Kaki Raveendra ;

He, Xin ;

Xu, Silong .

SYNLETT, 2020, 31 (02) :117-124

[8] Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes [J].

Ben Hay, E. ;

Zhang, Hanmo ;

Curran, Dennis P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :322-327

[9] Palladium-catalyzed [3C+2C+2C] cycloaddition of enynylidenecyclopropanes: efficient construction of fused 5-7-5 tricyclic systems [J].

Bhargava, Gaurav ;

Trillo, Beatriz ;

Araya, Marisel ;

Lopez, Fernando ;

Castedo, Luis ;

Mascarenas, Jose L. .

CHEMICAL COMMUNICATIONS, 2010, 46 (02) :270-272

[10]

Binger P, 1998, EUR J ORG CHEM, V1998, P113

← 1 2 3 4 5 6 7 8 9 10 →