synthesis with perfect atom economy: generation of furan derivatives by 1,3-dipolar cycloaddition of acetylenedicarboxylates at cyclooctynes
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ID: 131990
2014
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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 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.
| Reference Key |
banert2014moleculessynthesis
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|---|---|
| Authors | ;Klaus Banert;Sandra Bochmann;Andreas Ihle;Oliver Plefka;Florian Taubert;Tina Walther;Marcus Korb;Tobias Rüffer;Heinrich Lang |
| Journal | Journal of ethnopharmacology |
| Year | 2014 |
| DOI |
10.3390/molecules190914022
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| URL | |
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