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
Aoyagi, Shigenobu
Kikuchi, Kazuma
Shimada, Kazuaki
Takikawa, Yuji
[J]. SYNLETT, 2007, (16) : 2553 - 2556
[2] 1,2-DIPHENYL-3-AZANAPHTHO[B]CYCLOBUTADIENE
ARDAKANI, AA
MALEKI, N
SAADEIN, MR
[J]. 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
Bai, Yihui
Yin, Jing
Liu, Zhicheng
Zhu, Gangguo
[J]. 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
Chai, Guobi
Wu, Shangze
Fu, Chunling
Ma, Shengming
[J]. 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
Chen, Ling
Yu, Lian
Deng, Yuan
Zheng, Zhan-Jiang
Xu, Zheng
Cao, Jian
Xu, Li-Wen
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) : 480 - 485
[6] Synthesis of α-haloenamides via zinc halide mediated direct addition of benzhydryl halides to ynamides
Chen, Ling
Yu, Lian
Deng, Yuan
Cui, Yuming
Bian, Gaofeng
Cao, Jian
[J]. 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
Chen, Peng-hao
Xu, Tao
Dong, Guangbin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) : 1674 - 1678
[9] Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides
Couty, Sylvain
Meyer, Christophe
Cossy, Janine
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) : 6726 - 6730
[10] Gold-catalyzed cycloisomerizations of ene-ynamides
Couty, Sylvain
Meyer, Christophe
Cossy, Janine
[J]. TETRAHEDRON, 2009, 65 (09) : 1809 - 1832

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