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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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
02 January 2019
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| In: |
Angewandte Chemie. International edition
Year: 2019, Volume: 58, Issue: 11, Pages: 3589-3593 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201812002 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1002/anie.201812002 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201812002 
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| Author Notes: | Xianhai Tian, Lina Song, Matthias Rudolph, Frank Rominger, Thomas Oeser, and A. Stephen K. Hashmi |
| Summary: | 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. |
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| Item Description: | Gesehen am 27.05.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201812002 |