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

被引：21
作者：
Artigas, Albert [1 ]
Vila, Jordi [1 ]
Lledo, Agusti [1 ]
Sola, Miguel [1 ,2 ]
Pla-Quintana, Anna [1 ]
Roglans, Anna [1 ,2 ]
机构：
[1] Univ Girona UdG, IQCC, C Maria Aurelia Co 69, Girona 17003, Catalunya, Spain
[2] Univ Girona UdG, Dept Quim, C Maria Aurelia Co 69, Girona 17003, Catalunya, Spain
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 17期
关键词：
2+2+2 CYCLOADDITION; CYCLIZATION REACTIONS; CHIRAL INDUCTION; ALLENES; DERIVATIVES; SCAFFOLDS; ACCESS;
D O I：
10.1021/acs.orglett.9b02032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encom-passes an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reactive cycloheptadiene, which concomitantly undergoes a regioselective [4 + 2] cyclo-addition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methods.
引用
收藏
页码：6608 / 6613
页数：6
相关论文
共 45 条
[1]   Beyond the Five and Six: Evaluation of Seven-Membered Cyclic Anhydrides in the Castagnoli-Cushman Reaction [J].
Adamovskyi, Mykhailo I. ;
Ryabukhin, Sergey V. ;
Sibgatulin, Dmitriy A. ;
Rusanov, Eduard ;
Grygorenko, Oleksandr O. .
ORGANIC LETTERS, 2017, 19 (01) :130-133
[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]   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
[4]   Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene-Ene-Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism [J].
Cassu, Daniel ;
Parella, Teodor ;
Sola, Miquel ;
Pla-Quintana, Anna ;
Roglans, Anna .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (59) :14889-14899
[5]   The Diversified Reactivities of 1,5-Bisallenes [J].
Chen, Guofei ;
Jiang, Xuefeng ;
Fu, Chunling ;
Ma, Shengming .
CHEMISTRY LETTERS, 2010, 39 (02) :78-81
[6]   Chiral Induction in Intramolecular Rhodium-Catalyzed [2+2+2] Cycloadditions of Optically Active Allene-ene/yne-allene Substrates [J].
Haraburda, Ewelina ;
Fernandez, Marti ;
Gifreu, Anna ;
Garcia, Jordi ;
Parella, Teodor ;
Pla-Quintana, Anna ;
Roglans, Anna .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (03) :506-512
[7]   Dehydrogenative [2+2+2] Cycloaddition of Cyano-yne-allene Substrates: Convenient Access to 2,6-Naphthyridine Scaffolds [J].
Haraburda, Ewelina ;
Liedo, Agusti ;
Roglans, Anna ;
Pla-Quintana, Anna .
ORGANIC LETTERS, 2015, 17 (12) :2882-2885
[8]   Stereoselective Rhodium-Catalysed [2+2+2] Cycloaddition of Linear Allene-Ene/Yne-Allene Substrates: Reactivity and Theoretical Mechanistic Studies [J].
Haraburda, Ewelina ;
Torres, Oscar ;
Parella, Teodor ;
Sola, Miquel ;
Pla-Quintana, Anna .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (17) :5034-5045
[9]   A stereoselective carbocyclization of bis(allenes) with germylstannane catalyzed by palladium complexes [J].
Hong, YT ;
Yoon, SK ;
Kang, SK ;
Yu, CM .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (22) :4628-4635
[10]   Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis(allene)s: Bicyclo[6.3.0]undecadienones and Bicyclo[5.3.0]decadienones [J].
Inagaki, Fuyuhiko ;
Narita, Syu ;
Hasegawa, Takuma ;
Kitagaki, Shinji ;
Mukai, Chisato .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (11) :2007-2011
12345