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Molecules 2014, 19(9), 14022-14035; doi:10.3390/molecules190914022

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

1
Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany
2
Inorganic Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany
*
Author to whom correspondence should be addressed.
Received: 1 August 2014 / Revised: 28 August 2014 / Accepted: 1 September 2014 / Published: 5 September 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
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Abstract

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 3bd, orthoesters 4ac, 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. View Full-Text
Keywords: cascade reactions; cyclopropenes; Diels-Alder reactions; dipolar intermediates; epoxides; orthoesters; oxygen heterocycles; reaction mechanisms; retro-Brook reactions; strained compounds cascade reactions; cyclopropenes; Diels-Alder reactions; dipolar intermediates; epoxides; orthoesters; oxygen heterocycles; reaction mechanisms; retro-Brook reactions; strained compounds
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Banert, 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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