Copper-Catalyzed Tandem Cross-Coupling/[2+2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems

被引：25

作者：

He, Min ^{[1
]}

Chen, Nuan ^{[1
]}

Zhou, Ting ^{[1
]}

Li, Qing ^{[1
]}

Li, Hongguang ^{[1
]}

Lang, Ming ^{[1
]}

Wang, Jian ^{[1
,2
]}

Peng, Shiyong ^{[1
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China

[2] Tsinghua Univ, Minist Educ, Key Lab Bioorgan Phosphorous Chem & Chem Biol, Sch Pharmaceut Sci, Beijing 100084, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

关键词：

TERMINAL ALKYNES; ASYMMETRIC-SYNTHESIS; ALLENES; CYCLOISOMERIZATIONS; HETEROCYCLES; DIAZOESTERS; REACTIVITY; ALLENOATES; INSERTION; CARBENES;

D O I：

10.1021/acs.orglett.9b03727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[S.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.

引用

页码：9559 / 9563

页数：5

共 54 条

[1] Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816

[2] Cyclization reactions of bis(allenes) for the synthesis of polycarbo(hetero) cycles [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :3106-3135

[3] Generating Complexity from Simplicity: Pd-Catalyzed or Cu-Promoted Domino Alkyne Homocoupling/Double [2+2] Allenyne Cycloaddition [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) :9987-9989

[4] A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles [J].

Artigas, Albert ;

Vila, Jordi ;

Lledo, Agusti ;

Sola, Miguel ;

Pla-Quintana, Anna ;

Roglans, Anna .

ORGANIC LETTERS, 2019, 21 (17) :6608-6613

[5] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].

Aubert, Corinne ;

Fensterbank, Louis ;

Garcia, Pierre ;

Malacria, Max ;

Simonneau, Antoine .

CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993

[6] Iron-catalyzed [2π+2π] cycloaddition of α,ω-dienes:: The importance of redox-active supporting ligands [J].

Bouwkamp, Marco W. ;

Bowman, Amanda C. ;

Lobkovsky, Emil ;

Chirik, Paul J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13340-13341

[7] A direct synthesis of alkenyl alkylidene bicyclo[3.1.0]hexane derivatives via ruthenium(II)-catalysed bicyclisation of allenynes [J].

Bray, Chloe Vovard-Le ;

Derien, Sylvie ;

Dixneuf, Pierre H. ;

Murakami, Masahiro .

SYNLETT, 2008, (02) :193-196

[8] Electrophilic activation of allenenes and allenynes: analogies and differences between Bronsted and Lewis acid activation [J].

Caneque, Tatiana ;

Truscott, Fiona Mary ;

Rodriguez, Raphael ;

Maestri, Giovanni ;

Malacria, Max .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :2916-2926

[9] Metal-Catalyzed Cross-Coupling of Terminal Alkynes with Different Carbene Precursors [J].

Che, Jiuwei ;

Xing, Dong ;

Hu, Wenhao .

CURRENT ORGANIC CHEMISTRY, 2016, 20 (01) :41-60

[10] Cycloaddition reactions of enoldiazo compounds [J].

Cheng, Qing-Qing ;

Deng, Yongming ;

Lankelma, Marianne ;

Doyle, Michael P. .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (17) :5425-5443

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