Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers: synthesis of alkylidenecyclobutenones and their reactivity in ring-opening and ring expansion

被引：20

作者：

Chen, Ling ^{[1
]}

Cao, Jian ^{[1
]}

Xu, Zheng ^{[1
]}

Zheng, Zhan-Jiang ^{[1
]}

Cui, Yu-Ming ^{[1
]}

Xu, Li-Wen ^{[1
,2
]}

机构：

[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, 1378 Wenyi West Rd,Sci Pk HZNU, Hangzhou 311121, Zhejiang, Peoples R China

[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, LICP, Beijing 100864, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 61期

基金：

中国国家自然科学基金;

关键词：

ORGANIC-SYNTHESIS; BOND ACTIVATION; ENE-YNAMIDES; DERIVATIVES; CYCLOBUTENONES; KETENES; BENZOCYCLOBUTENONES; CYCLOISOMERIZATIONS; BENZANNULATION; ALLENYLKETENES;

D O I：

10.1039/c6cc04648g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A family of four-membered enones, polysubstituted alkylidenecyclo-butenones, were easily prepared by a Lewis acid catalyzed [2+2] cycloaddition of ynamides and propargyl silyl ethers. This challenging regioselective [2+2] cycloaddition enables the efficient construction and conversion of four-membered enones, which provides high-value and structurally diverse products through the unexpected ring-opening and ring expansion of alkylidenecyclobutenone with Grignard reagents, organolithium, primary amines, and water.

引用

页码：9574 / 9577

页数：4

共 48 条

[1] Convenient synthesis of 4-methylenecyclobutenones and their synthetic utility as allenylketene precursors [J].

Aoyagi, Shigenobu ;

Kikuchi, Kazuma ;

Shimada, Kazuaki ;

Takikawa, Yuji .

SYNLETT, 2007, (16) :2553-2556

[2] 1,2-DIPHENYL-3-AZANAPHTHO[B]CYCLOBUTADIENE [J].

ARDAKANI, AA ;

MALEKI, N ;

SAADEIN, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4128-4131

[3] Construction of 1-Naphthols via Benzannulation Based on the Reaction of Aryl tert-Butyl Ynol Ethers with Ynamides or Ynol Ethers [J].

Bai, Yihui ;

Yin, Jing ;

Liu, Zhicheng ;

Zhu, Gangguo .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) :10226-10233

[4] A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs [J].

Chai, Guobi ;

Wu, Shangze ;

Fu, Chunling ;

Ma, Shengming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3740-3743

[5] C-H Functionalization/C-O Bond Cleavage of Benzyl Silyl Ethers with Ynamides for the Chemoselective Synthesis of Skeletally Diverse Compounds [J].

Chen, Ling ;

Yu, Lian ;

Deng, Yuan ;

Zheng, Zhan-Jiang ;

Xu, Zheng ;

Cao, Jian ;

Xu, Li-Wen .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) :480-485

[6] Synthesis of α-haloenamides via zinc halide mediated direct addition of benzhydryl halides to ynamides [J].

Chen, Ling ;

Yu, Lian ;

Deng, Yuan ;

Cui, Yuming ;

Bian, Gaofeng ;

Cao, Jian .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (02) :564-569

[7]

Chen PH, 2015, CHEM SCI, V6, P5440, DOI [10.1039/C5SC01875G, 10.1039/c5sc01875g]

[8] Divergent Syntheses of Fused β-Naphthol and Indene Scaffolds by Rhodium-Catalyzed Direct and Decarbonylative Alkyne-Benzocyclobutenone Couplings [J].

Chen, Peng-hao ;

Xu, Tao ;

Dong, Guangbin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1674-1678

[9] Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730

[10] Gold-catalyzed cycloisomerizations of ene-ynamides [J].

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

TETRAHEDRON, 2009, 65 (09) :1809-1832

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