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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:bsz:ch1-qucosa-152891
Date25 September 2014
CreatorsBanert, Klaus, Bochmann, Sandra, Ihle, Andreas, Plefka, Oliver, Taubert, Florian, Walther, Tina, Korb, Marcus, Rüffer, Tobias, Lang, Heinrich
ContributorsMDPI AG,, Technische Universität Chemnitz, Fakultät für Naturwissenschaften, Technische Universität Chemnitz, Fakultät für Naturwissenschaften, Technische Universität Chemnitz, Fakultät für Naturwissenschaften
PublisherUniversitätsbibliothek Chemnitz
Source SetsHochschulschriftenserver (HSSS) der SLUB Dresden
LanguageEnglish
Detected LanguageEnglish
Typedoc-type:article
Formatapplication/pdf, text/plain, application/zip
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

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