α-Imino gold carbenes from 1,2,4-oxadiazoles: atom-economical access to fully substituted 4-aminoimidazoles
A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular t...
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| Main Authors: | , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
February 20, 2017
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| In: |
Organic letters
Year: 2017, Volume: 19, Issue: 5, Pages: 1020-1023 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/acs.orglett.7b00001 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1021/acs.orglett.7b00001
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| Author Notes: | Zhongyi Zeng, Hongming Jin, Jin Xie, Bing Tian, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi |
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| 520 | |a A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale. | ||
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