Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines

We herein report the gold(III)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the g...

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Main Authors: Song, Lina (Author) , Tian, Xianhai (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 28 Jun 2019
In: Chemical communications
Year: 2019, Volume: 55, Issue: 61, Pages: 9007-9010
ISSN:1364-548X
DOI:10.1039/C9CC04027G
Online Access:Resolving-System, Volltext: https://doi.org/10.1039/C9CC04027G
Verlag: https://pubs.rsc.org/en/content/articlelanding/2019/cc/c9cc04027g
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Author Notes:Lina Song, Xianhai Tian, Matthias Rudolph, Frank Rominger and A. Stephen K. Hashmi
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Summary:We herein report the gold(III)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).
Item Description:Gesehen am 06.11.2019
Physical Description:Online Resource
ISSN:1364-548X
DOI:10.1039/C9CC04027G