| |  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)
