| Online-Ressource |
Verfasst von: | Tian, Xianhai [VerfasserIn]  |
| Song, Lina [VerfasserIn]  |
| Rudolph, Matthias [VerfasserIn]  |
| Rominger, Frank [VerfasserIn]  |
| Oeser, Thomas [VerfasserIn]  |
| Hashmi, A. Stephen K. [VerfasserIn]  |
Titel: | Sulfilimines as versatile nitrene transfer reagents |
Titelzusatz: | facile access to diverse aza-heterocycles |
Verf.angabe: | Xianhai Tian, Lina Song, Matthias Rudolph, Frank Rominger, Thomas Oeser, and A. Stephen K. Hashmi |
E-Jahr: | 2019 |
Jahr: | 02 January 2019 |
Umfang: | 4 S. |
Teil: | volume:58 |
| year:2019 |
| number:11 |
| pages:3589-3593 |
| extent:4 |
Fussnoten: | Gesehen am 27.05.2019 |
Titel Quelle: | Enthalten in: Angewandte Chemie / International edition |
Ort Quelle: | Weinheim : Wiley-VCH, 1962 |
Jahr Quelle: | 2019 |
Band/Heft Quelle: | 58(2019), 11, Seite 3589-3593 |
ISSN Quelle: | 1521-3773 |
Abstract: | 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. |
DOI: | doi:10.1002/anie.201812002 |
URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Volltext ; Verlag: https://doi.org/10.1002/anie.201812002 |
| Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201812002 |
| DOI: https://doi.org/10.1002/anie.201812002 |
Datenträger: | Online-Ressource |
Sprache: | eng |
Sach-SW: | C−H annulation |
| cyclopropanation |
| gold carbenes |
| gold catalysis |
| sulfilimines |
K10plus-PPN: | 1666338818 |
Verknüpfungen: | → Zeitschrift |
Sulfilimines as versatile nitrene transfer reagents / Tian, Xianhai [VerfasserIn]; 02 January 2019 (Online-Ressource)