| Intermolecular reaction of internal alkynes and imines: propargyl tosylates as key partners in a gold-catalyzed [4 + 1] unusual cyclization leading to cyclopent-2-enimines. | |
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MedLine Citation:
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PMID: 19046069 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Propargyl tosylates react with N-tosylaldimines to afford cyclopent-2-enimines in a gold-catalyzed process that involves a deep reorganization of both substrates. The formal [4 + 1] cyclization is initiated by a 1,2-migration of the tosylate that eventually generates a substituted 1,3-diene. Subsequent interaction with the imine launches a series of reaction steps prior to a Nazarov-like cyclization to yield the final product. |
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Authors:
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Samuel Suárez-Pantiga; Eduardo Rubio; Carmen Alvarez-Rúa; José M González |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic letters Volume: 11 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2009 Jan |
Date Detail:
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Created Date: 2009-01-02 Completed Date: 2009-02-10 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 13-6 Citation Subset: IM |
Affiliation:
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Instituto Universitario de Química Organometálica Enrique Moles-Unidad Asociada al C.S.I.C. and Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Claveria, 8, 33006 Oviedo, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkynes
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chemistry* Catalysis Cyclization Gold / chemistry* Imines / chemical synthesis*, chemistry* Molecular Structure Stereoisomerism Tosyl Compounds / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Alkynes; 0/Imines; 0/Tosyl Compounds; 7440-57-5/Gold |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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