Cycloaddition and Annulation Reactions of Donor–Acceptor Cyclopropanes

废止 环加成 化学 接受者 立体化学 药物化学 光化学 有机化学 物理 催化作用 凝聚态物理
作者
Роман А. Новиков,Denis D. Borisov,Yury V. Tomilov
标识
DOI:10.1002/9783527835652.ch3
摘要

Chapter 3 Cycloaddition and Annulation Reactions of Donor–Acceptor Cyclopropanes Roman A. Novikov, Roman A. Novikov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this authorDenis D. Borisov,, Denis D. Borisov, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this authorYury V. Tomilov, Yury V. Tomilov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this author Roman A. Novikov, Roman A. Novikov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this authorDenis D. Borisov,, Denis D. Borisov, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this authorYury V. Tomilov, Yury V. Tomilov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationSearch for more papers by this author Book Editor(s):Akkattu Biju, Akkattu Biju Indian Institute of Science, Bangalore, 560012 IndiaSearch for more papers by this authorPrabal Banerjee, Prabal Banerjee Indian Institute Technology, Ropar, 140001 IndiaSearch for more papers by this author First published: 16 February 2024 https://doi.org/10.1002/9783527835652.ch3 AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary Cycloaddition reactions are the most studied reactions of donor–acceptor cyclopropanes in any category. The polarization of the activated carbon-carbon bond of the donor–acceptor cyclopropane (DAC) makes it a perfect synthon for a 1,3-zwitterionic intermediate on activation. So far, the most common activator that has been exploited for the activation of DACs toward formal cycloaddition/annulation reactions is the metal-based Lewis acids. However, a number of methods developed for such cyclization processes also involved metal-free activators. In addition to the 1,3-zwitterionic intermediate, various DACs are also known to serve as precursors for styryl malonates and 1,2-zwitterionic intermediates. Also, there are some examples where DACs act as sources of 1,3- and 1,4-zwitterionic species by using the aryl donor as part of the zwitterionic subunit. Consequently, DACs are known to undergo numerous formal cycloaddition/annulation processes with diverse reacting partners involving C–C and carbon–heteroatom multiple bonds, as well as with many other dipolar species discussed in the domain of this chapter. References Reissig , H.U. and Zimmer , R. ( 2003 ). Chem. 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