Electrophilic activation of allenenes and allenynes: analogies and differences between Bronsted and Lewis acid activation

被引：55

作者：

Caneque, Tatiana ^{[1
]}

Truscott, Fiona Mary ^{[1
]}

Rodriguez, Raphael ^{[1
]}

Maestri, Giovanni ^{[1
,2
]}

Malacria, Max ^{[1
,3
]}

机构：

[1] CNRS, ICNS UPR2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Univ Parma, Dipartimento Chim, I-43124 Parma, Italy

[3] Univ Paris 06, IPCM UMR, Inst Parisienne Chim Mol, F-75005 Paris, France

来源：

CHEMICAL SOCIETY REVIEWS | 2014年 / 43卷 / 09期

关键词：

GOLD-CATALYZED CYCLOISOMERIZATION; NAZAROV CYCLIZATION; ASYMMETRIC CYCLOPENTANNELATION; CHIRAL AUXILIARY; INTRAMOLECULAR CYCLOADDITION; 1,5-ALLENYNES; CARBOCYCLIZATION; STEREOCHEMISTRY; ALLENEDIENES; GENERATION;

D O I：

10.1039/c4cs00023d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Tutorial Review summarizes recent examples of electrophilic activation of allenes with particular focus on analogies and differences between Lewis and Bronsted acid activation of these versatile substrates. The aim of this article is to present a general overview of the possibilities offered to chemists using complementary modes of catalysis and to emphasize advantages and limitations of each approach, thereby providing a means to expand the scope of this powerful synthetic methodology.

引用

页码：2916 / 2926

页数：11

共 51 条

[1] Carbocyclization versus Oxycyclization on the Metal-Catalyzed Reactions of Oxyallenyl C3-Linked Indoles [J].

Alcaide, Benito ;

Almendros, Pedro ;

Alonso, Jose M. ;

Fernandez, Israel .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13) :6688-6701

[2] Gold- or Palladium-Catalyzed Allene Carbocyclization/Functionalization: Simple and Efficient Synthesis of Carbazoles [J].

Alcaide, Benito ;

Almendros, Pedro ;

Alonso, Jose M. ;

Teresa Quiros, M. ;

Gadzinski, Pawel .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1871-1876

[3] Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].

Alonso, Isaac ;

Trillo, Beatriz ;

Lopez, Fernando ;

Montserrat, Sergi ;

Ujaque, Gregori ;

Castedo, Luis ;

Lledos, Agusti ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030

[4] Regioselective Synthesis of Elusive 4,9-Dihydro-1H-Carbazoles by Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles [J].

Alvarez, Estela ;

Garcia-Garcia, Patricia ;

Fernandez-Rodriguez, Manuel A. ;

Sanz, Roberto .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9758-9771

[5]

[Anonymous], 2013, ANGEW CHEM INT EDIT

[6] Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization [J].

Banaag, April R. ;

Tius, Marcus A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8133-8141

[7] Convergent cyclopentannelation process [J].

Bee, C ;

Tius, MA .

ORGANIC LETTERS, 2003, 5 (10) :1681-1684

[8] Terpestacin core structure. Control of stereochemistry [J].

Berger, GO ;

Tius, MA .

ORGANIC LETTERS, 2005, 7 (22) :5011-5013

[9] Gold-Catalyzed 1,3-Addition of a Sp3-Hybridized C-H Bond to Alkenylcarbenoid Intermediate [J].

Bhunia, Sabyasachi ;

Liu, Rai-Shung .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) :16488-+

[10] Gold-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Aryl-1-allene-6-enes [J].

Chaudhuri, Rupsha ;

Liao, Hsin-Yi ;

Liu, Rai-Shung .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (35) :8895-8901

← 1 2 3 4 5 6 →