Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds
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Título: | Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds |
Autor/a: | Varela Sandá, Iván Faustino, Hélio Díez Martín, Elena Iglesias Sigüenza, Francisco Javier Grande-Carmona, Francisca Fernández, Rosario Lassaletta, José M. Mascareñas Cid, José Luis López García, Fernando |
Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Palabras chave: | Allenamide | Cycloaddition | Enantioselective synthesis | Gold catalysis | N-heterocyclic carbenes | Tetrahydropyrans | |
Data: | 2017-02-22 |
Editor: | American Chemical Society |
Cita bibliográfica: | Varela, Iván, Faustino, Hélio, Díez, Elena, Iglesias-Sigüenza, Javier, Grande-Carmona, Francisca, Fernández, Rosario, Lassaletta, José M., Mascareñas, José L. and López, Fernando, 2017, Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds. ACS Catalysis. 2017. Vol. 7, no. 4, p. 2397-2402. DOI 10.1021/acscatal.6b03651. American Chemical Society (ACS) |
Resumo: | A straightforward and atom-economical enantioselective approach to highly substituted tetrahydropyrans is reported. The process, which consists of an intermolecular gold-catalyzed [2+2+2] cycloaddition between allenamides, alkenes, and aldehydes, is efficiently catalyzed by both phosphoramidite- and chiral N-heterocyclic carbene-gold catalysts, occurs with complete chemoselectivity and regioselectivity, moderate diastereoselectivity, and moderate to very good enantioselectivities |
Descrición: | This is the peer reviewed version of the following article: Iván Varela, Hélio Faustino, Elena Díez, Javier Iglesias-Sigüenza, Francisca Grande-Carmona, Rosario Fernández, José M. Lassaletta, José L. Mascareñas* and Fernando López*, Gold (I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds. ACS Catal. 2017, 7, 2397-2402 [DOI: 10.1021/acscatal.6b03651]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving |
Versión do editor: | http://dx.doi.org/10.1021/acscatal.6b03651 |
URI: | http://hdl.handle.net/10347/15445 |
DOI: | 10.1021/acscatal.6b03651 |
E-ISSN: | 2155-5435 |
Dereitos: | © 2017 American Chemical Society |
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