Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds

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URI: http://hdl.handle.net/10347/15445
E-ISSN: 2155-5435
DOI: 10.1021/acscatal.6b03651

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2017-02-22

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American Chemical Society
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Abstract

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

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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

Keywords

Allenamide| Cycloaddition| Enantioselective synthesis| Gold catalysis| N-heterocyclic carbenes| Tetrahydropyrans

Bibliographic citation

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)

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This work was supported by the Spanish MINECO (grant:SAF2013-41943-R, CTQ2013-48164-C2-1-P and -2-P), the Consellería de Cultura, Educación e Ordenación Universitaria (GRC2013-041, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2016-2019, ED431G/09) the European Regional Development Fund (ERDF), the European Research Council (Adv. Grant No. 340055), and the Junta de Andalucía (Grant 2012/FQM 1078). We also thank the Orfeo-Cinqa network

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© 2017 American Chemical Society

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Química Orgánica