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Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes

Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b–d, orthoesters 4a–c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy.

Identiferoai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:20123
Date25 September 2014
CreatorsBanert, Klaus, Bochmann, Sandra, Ihle, Andreas, Plefka, Oliver, Taubert, Florian, Walther, Tina, Korb, Marcus, Rüffer, Tobias, Lang, Heinrich
ContributorsTechnische Universität Chemnitz
PublisherMDPI AG
Source SetsHochschulschriftenserver (HSSS) der SLUB Dresden
LanguageEnglish
Detected LanguageEnglish
Typedoc-type:article, info:eu-repo/semantics/article, doc-type:Text
SourceBanert, K.; Bochmann, S.; Ihle, A.; Plefka, O.; Taubert, F.; Walther, T.; Korb, M.; Rüffer, T.; Lang, H. Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes. Molecules 2014, 19, 14022-14035
Rightsinfo:eu-repo/semantics/openAccess
Relation10.3390/molecules190914022, 1420-3049

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