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Sulfilimines as versatile nitrene transfer reagents: facile access to diverse aza-heterocycles

We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of...

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Hauptverfasser: Tian, Xianhai (VerfasserIn) , Song, Lina (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Oeser, Thomas (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 02 January 2019
In: Angewandte Chemie. International edition
Year: 2019, Jahrgang: 58, Heft: 11, Pages: 3589-3593
ISSN:1521-3773
DOI:10.1002/anie.201812002
Online-Zugang:Verlag, Volltext: https://doi.org/10.1002/anie.201812002
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201812002
Volltext
Verfasserangaben:Xianhai Tian, Lina Song, Matthias Rudolph, Frank Rominger, Thomas Oeser, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α-imino gold carbenes by N−S cleavage of sulfilimines. These gold carbenes undergo C−H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3-azabicyclo[3.1.0]hexan-2-imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold-catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza-heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α-imino gold carbenes. Moreover, an unexpected synthesis of 4-acylquinolines (3 examples) from 2-acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2-hydride shift onto the α-imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered.
Beschreibung:Gesehen am 27.05.2019
Beschreibung:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201812002

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