Addition Reactions: Cycloaddition

Chapter 10 Addition Reactions: Cycloaddition N. Dennis, N. Dennis Stretton, Queensland, AustraliaSearch for more papers by this author N. Dennis, N. Dennis Stretton, Queensland, AustraliaSearch for more papers by this author Book Editor(s):Mark Moloney, Mark Moloney University of Oxford, Mansfield Road, Oxford, UK, OX1 3TA United KingdomSearch for more papers by this author First published: 15 March 2024 https://doi.org/10.1002/9781119716846.ch10Book Series:Organic Reaction Mechanisms Series AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary A review describing the synthesis of chiral spirooxindoles with quaternary stereogenic centers via 1,3-dipolar cycloaddition, Diels–Alder, and nucleophilic heterocyclic carbene reactions has been reported. A review of the synthesis of isoxazolines via iminoyl radical-initiated intramolecular cyclization, intermolecular radical addition-initiated cyclization, intramolecular nucleophilic cyclization, [3+2]-cycloaddition, and [2+2+1]-cycloaddition is presented. Molecular electron density theory (MEDT) investigations of the [3+2]-cycloaddition reactions of E-azomethine imines and 2-sulfolene show that the reaction follows a non-concerted two-stage one-step molecular mechanism. MEDT has been used to investigate the Grignard reagent-mediated [3+2]-cycloaddition reaction of phenyl azide with ethynylbenzene in the presence of ethyl magnesium bromide. References Ramirez , M. , Li , W. F. , Lam , Y. H. , Ghosez , L. , and Houk , K. N. , J. Org. Chem. , 85 , 2597 ( 2020 ). 10.1021/acs.joc.9b03340 CASPubMedWeb of Science®Google Scholar Shi , Y. J. , Liu , X. J. , Han , Y. , Yan , P. , Bie , F. S. , and Cao , H. , Tetrahedron Lett. , 61 , 151752 ( 2020 ). Google Scholar McVeigh , M. 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