Status: Bibliographieeintrag
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| Verfasst von: | Hashmi, A. Stephen K. [VerfasserIn]  |
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| | Schuster, Andreas M. [VerfasserIn] |
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| | Schmuck, Martin [VerfasserIn] |
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| | Rominger, Frank [VerfasserIn] |
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| Titel: | Gold-catalyzed cyclization of nonterminal propargylic amides to substituted alkylideneoxazolines and -oxazines |
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| Verf.angabe: | A. Stephen K. Hashmi, Andreas M. Schuster, Martin Schmuck, and Frank Rominger |
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| E-Jahr: | 2011 |
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| Jahr: | 22 June 2011 |
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| Umfang: | 8 S. |
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| Fussnoten: | Gesehen am 07.09.2022 |
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| Titel Quelle: | Enthalten in: European journal of organic chemistry |
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| Ort Quelle: | Weinheim : Wiley-VCH Verl., 1998 |
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| Jahr Quelle: | 2011 |
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| Band/Heft Quelle: | (2011), 24, Seite 4595-4602 |
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| ISSN Quelle: | 1099-0690 |
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| Abstract: | The substrate scope of the gold-catalyzed cyclization of nonterminal propargylic amides to oxazolines and oxazines was investigated. Sixteen alkyl-substituted and 35 aryl-substited substrates were prepared by a very variable route from trimethylsilyl-(TMS-)protected, nonterminal propargylamines. Steric and electronic influences of the substituents on product selectivity were studied. A chloromethyl substituent on the alkyne shows an efficient 1,4-elimination to deliver vinyloxazoles. A second alkynyl group, tethered to the alkyl group at the alkyne, in some cases led to a gold catalysis/Alder-ene domino reaction. With Barluenga's reagent the iodoalkylideneoxazoline can be formed in excellent yield. In contrast to the palladium-catalyzed protocols, the gold-catalyzed conditions for the cyclization of nonterminal propargylic amides are much milder, thus, for example, no special precautions are needed to prevent isomerization of the oxazolines to the aromatic oxazoles. |
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| DOI: | doi:10.1002/ejoc.201100342 |
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| 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/ejoc.201100342 |
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| | Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201100342 |
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| | DOI: https://doi.org/10.1002/ejoc.201100342 |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| Bibliogr. Hinweis: | Erscheint auch als : Druck-Ausgabe: Gold-catalyzed cyclization of nonterminal propargylic amides to substituted alkylidene oxazolines and oxazines. - 2011 |
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| Sach-SW: | Alder-ene reaction |
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| | Alkynes |
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| | Amides |
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| | Cyclization |
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| | Gold |
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| | Oxazines |
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| | Oxazoles |
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| K10plus-PPN: | 181599214X |
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| Verknüpfungen: | → Zeitschrift |
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Gold-catalyzed cyclization of nonterminal propargylic amides to substituted alkylideneoxazolines and -oxazines / Hashmi, A. Stephen K. [VerfasserIn]; 22 June 2011 (Online-Ressource)
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