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Synthesis of highly substituted 3-formylfurans by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade

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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 e...

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Bibliographic Details
Main Authors: Wang, Tao (Author) , Shi, Shuai (Author) , Hansmann, Max M. (Author) , Rettenmeier, Eva (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: February 24, 2014
In: Angewandte Chemie. International edition
Year: 2014, Volume: 53, Issue: 14, Pages: 3715-3719
ISSN:1521-3773
DOI:10.1002/anie.201310146
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/anie.201310146
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201310146
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Author Notes:Tao Wang, Shuai Shi, Max M. Hansmann, Eva Rettenmeier, Matthias Rudolph, and A. Stephen K. Hashmi
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Summary: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.
Item Description:Gesehen am 29.07.2020
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201310146

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