Rhodium(III)‐Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents

作者: Takanori Matsuda , Kentaro Suzuki

DOI: 10.1002/EJOC.201500252

关键词:

摘要: Substituted maleic anhydrides function as synthetic equivalents of alkynes in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve formal [2+2+2] cyclotrimerization. This approach is useful for reactions involving low boiling points or severe ring strain. Hard-to-access cycloadducts are available through this new cycloaddition strategy by employing easy-to-handle alkyne equivalents.

参考文章(35)
Yuna Sato, Kouji Kuramochi, Takahiro Suzuki, Atsuo Nakazaki, Susumu Kobayashi, The second generation synthesis of (+)-pseudodeflectusin Tetrahedron Letters. ,vol. 52, pp. 626- 629 ,(2011) , 10.1016/J.TETLET.2010.11.153
Sambasivarao Kotha, Enugurthi Brahmachary, Kakali Lahiri, Transition Metal Catalyzed [2+2+2] Cycloaddition and Application in Organic Synthesis European Journal of Organic Chemistry. ,vol. 2005, pp. 4741- 4767 ,(2005) , 10.1002/EJOC.200500411
Christian Reus, Nai-Wei Liu, Michael Bolte, Hans-Wolfram Lerner, Matthias Wagner, Synthesis of bromo-, boryl-, and stannyl-functionalized 1,2-bis(trimethylsilyl)benzenes via Diels-Alder or C-H activation reactions. Journal of Organic Chemistry. ,vol. 77, pp. 3518- 3523 ,(2012) , 10.1021/JO3002936
Stéphane Perreault, Tomislav Rovis, Multi-component Cycloaddition Approaches in the Catalytic Asymmetric Synthesis of Alkaloid Targets Chemical Society Reviews. ,vol. 38, pp. 3149- 3159 ,(2009) , 10.1039/B816702H
Damien F. Crépin, Joseph P. A. Harrity, Lewis Base Directed Cycloaddition Reactions of 2-Pyrones and Alkynylaluminum Reagents Organic Letters. ,vol. 15, pp. 4222- 4225 ,(2013) , 10.1021/OL401952K
Fangfang Fan, Jingjing Dong, Jinqian Wang, Lina Song, Chuanjun Song, Junbiao Chang, An Intramolecular Pyranone Diels-Alder Cycloaddition Approach to Cannabinol Advanced Synthesis & Catalysis. ,vol. 356, pp. 1337- 1342 ,(2014) , 10.1002/ADSC.201301037
Masaki Itoh, Masaki Shimizu, Koji Hirano, Tetsuya Satoh, Masahiro Miura, Rhodium-catalyzed decarboxylative and dehydrogenative coupling of maleic acids with alkynes and alkenes. Journal of Organic Chemistry. ,vol. 78, pp. 11427- 11432 ,(2013) , 10.1021/JO401992D
Denise A. Colby, Andy S. Tsai, Robert G. Bergman, Jonathan A. Ellman, Rhodium catalyzed chelation-assisted C-H bond functionalization reactions Accounts of Chemical Research. ,vol. 45, pp. 814- 825 ,(2012) , 10.1021/AR200190G
Jaime R. Cabrera-Pardo, David I. Chai, Song Liu, Milan Mrksich, Sergey A. Kozmin, Label-assisted mass spectrometry for the acceleration of reaction discovery and optimization Nature Chemistry. ,vol. 5, pp. 423- 427 ,(2013) , 10.1038/NCHEM.1612