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oai:riubu.ubu.es:10259/38932022-12-20T11:48:42Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Enantioselective Synthesis of Cyclopentadienes by Gold(I)- Catalyzed Cyclization of 1,3-Dien-5-ynes Sanjuán Cortázar, Ana María García García, Patricia Fernández Rodríguez, Manuel A. Sanz Díez, Roberto cycloisomerization cyclopentadienes Diels–Alder reaction dienynes gold Química orgánica Chemistry, Organic An asymmetric synthesis of elusive chiral cyclopentadienes has been developed by gold(I)-catalyzed alkoxycyclization of 1,3-dien-5-ynes. The application of these substrates in completely diastereoselective Diels–Alder cycloaddition reactions, which can be carried out in one pot from achiral 1,3-dien-5-ynes, allows the preparation of highly functionalized products bearing five stereogenic centers with high enantiomeric excesses Ministerio de Ciencia e Innovacion (MICINN) and FEDER (CTQ2010-15358 and CTQ2009-09949/BQU) and Junta de Castilla y Leon (BU021A09 and GR-172) for financial support. A. M. S. thanks Junta de Castilla y Leon (Consejeria de Educacion) and Fondo Social Europeo for a PIRTU contract. P. G.-G. and M. A. F.-R. thank MICINN for "Juan de la Cierva" and "Ramon y Cajal" contracts This is the peer reviewed version of the following article: Sanjuán, A. M., García-García, P., Fernández-Rodríguez, M. A. and Sanz, R. (2013), Enantioselective Synthesis of Cyclopentadienes by Gold(I)- Catalyzed Cyclization of 1,3-Dien-5-ynes. Adv. Synth. Catal., 355: 1955–1962. doi: 10.1002/adsc.201300448, which has been published in final form at 10.1002/adsc.201300448. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving 2015-12-10T10:56:51Z 2015-12-10T10:56:51Z 2013-07 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1615-4150 http://hdl.handle.net/10259/3893 10.1002/adsc.201300448 eng Advanced Synthesis & Catalysis. 2013, V. 355, n. 10, p. 1955–1962 http://dx.doi.org/10.1002/adsc.201300448 info:eu-repo/grantAgreement/MICINN/CTQ2010-15358 info:eu-repo/grantAgreement/MICINN/CTQ2009-09949/BQU info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/grantAgreement/JCyL/GR-172 info:eu-repo/semantics/openAccess application/pdf Wiley-VCH Verlag