Synthesis of Cyclobutanones by Gold(I)-Catalyzed [2+2] Cycloaddition of Ynol Ethers with Alkenes

被引：14

作者：

Zanini, Margherita ^{[1
,2
]}

Cataffo, Andrea ^{[1
,2
]}

Echavarren, Antonio M. ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[2] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 22期

关键词：

HALOGENATED KETENES; SCALABLE SYNTHESIS; RING EXPANSION; ALKYNES; CYCLOBUTENE;

D O I：

10.1021/acs.orglett.1c03499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broad scope synthesis of cyclobutanones by gold(I)-catalyzed [2 + 2] cycloaddition of ynol ethers with alkenes has been developed. We also found that internal aryl ynol ethers can undergo (4 + 2) cycloaddition reaction with alkenes leading to the corresponding chromanes.

引用

页码：8989 / 8993

页数：5

共 55 条

[1] Ketenes and Other Cumulenes as Reactive Intermediates [J].

Allen, Annette D. ;

Tidwell, Thomas T. .

CHEMICAL REVIEWS, 2013, 113 (09) :7287-7342

[2] Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes [J].

Bai, Yu-Bin ;

Luo, Zaigang ;

Wang, Yuguang ;

Gao, Jin-Ming ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (17) :5860-5865

[3] HALOGENATED KETENES .31. CYCLOADDITION OF DICHLOROKETENE WITH HINDERED OLEFINS [J].

BAK, DA ;

BRADY, WT .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 44 (01) :107-110

[4] Transannular cyclization of epoxycaryophyllenes catalyzed by TiIII:: An efficient synthesis of tricyclo[6.3.0.02,5]undecanes [J].

Barrero, Alejandro F. ;

Herrador, M. Mar ;

Quilez del Moral, Jose F. ;

Arteaga, Pilar ;

Sanchez, Elena M. ;

Arteaga, Jesus F. ;

Piedra, Maria .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (15) :3434-3441

[5] HALOGENATED KETENES .14. SUBSTITUDNT EFFECTS IN UNSYMMETRICAL ALKYLHALOKETENE - CYCLOPNTADIENE CYCLOADDITIONS [J].

BRADY, WT ;

ROE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) :4618-&

[6] HALOGENATED KETENES .I. DICHLOROKETENE [J].

BRADY, WT ;

LIDDELL, HG ;

VAUGHN, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :626-&

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

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

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

[8] Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes [J].

Dateer, Ramesh B. ;

Shaibu, Balagopal S. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :113-117

[9] Bioactive cyclobutane-containing alkaloids [J].

Dembitsky, Valery M. .

JOURNAL OF NATURAL MEDICINES, 2008, 62 (01) :1-33

[10] Catalytic Asymmetric [3+1]-Cycloaddition Reaction of Ylides with Electrophilic Metallo-enolcarbene Intermediates [J].

Deng, Yongming ;

Massey, Lynee A. ;

Zavalij, Peter Y. ;

Doyle, Michael P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) :7479-7483

← 1 2 3 4 5 6 →