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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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Bibliographic Details
Main Authors: Zeng, Zhongyi (Author) , Jin, Hongming (Author) , Xie, Jin (Author) , Tian, Bing (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: February 20, 2017
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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Summary: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.
Item Description:Gesehen am 28.08.2017
Physical Description:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.7b00001

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