Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 14, Pages 3715-3719Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310146
Keywords
alkynyl migration; cyclization; furans; gold; N-oxides
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Funding
- China Scholarship Council (CSC)
- Fonds der chemischen Industrie
- state of Baden-Wurttemberg via the Graduate Academy of Heidelberg University
- bwGRiD, member of the German D-Grid initiative - Ministry for Education and Research
- Ministry for Science, Research and Arts Baden-Wurttemberg
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3-Formylfuran derivatives are core structures of a variety of bioactive natural products. However, procedures for their preparation are still rare and generally inefficient in terms of atom economy: These methods require multiple steps or harsh reaction conditions and show selectivity problems. An efficient gold(I)-catalyzed cascade reaction that leads to 3-formylfurans from easily accessible starting materials is now described. A wide variety of 3-formylfurans were obtained from the corresponding symmetric and unsymmetric 1,4-diyn-3-ols in the presence of an N-oxide in good to excellent yields. Isotope-labeling experiments as well as DFT calculations support a mechanism in which, after an initial oxygen transfer, a 1,2-alkynyl migration is favored over a hydride shift; a cyclization ensues to afford the desired functionalized furan core.
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