2024-03-29T09:14:30Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/38952022-12-19T09:36:20Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenes
Sanjuán Cortázar, Ana María
Rashid, Muhammad A.
García García, Patricia
Martínez Cuezva, Alberto
Fernández Rodríguez, Manuel A.
Rodríguez, Félix
Sanz Díez, Roberto
asymmetric catalysis
cyclization
cycloisomerization
gold
indenes
Química orgánica
Chemistry, Organic
Indenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o-(alkynyl)-α-methylstyrenes from 6-endo to 5-endo was observed by adding an alcohol to the reaction media. This allowed the synthesis of interesting indenes bearing an all-carbon quaternary center at C1. Moreover, dihydrobenzo[a]fluorenes can be obtained from substrates bearing a secondary alkyl group at the β-position of the styrene moiety by a tandem cycloisomerization/1,2-hydride migration process. In addition, diverse polycyclic compounds were obtained by an intramolecular gold-catalyzed alkoxycyclization of o-(alkynyl)styrenes bearing a nucleophile in their structure. Finally, the use of a chiral gold complex allowed access to elusive chiral 1H-indenes in good enantioselectivities
Ministerio de Economia y Competitividad (MINECO) and FEDER (CTQ2010-15358 and CTQ2013-48937-C2-1-P) and Junta de Castilla y Leon (BU237U13) for financial support. A.M.S. thanks the Junta de Castilla y Leon (Consejeria de Educacion) and the Fondo Social Europeo for a PIRTU contract. M.A.R. and P.G.-G. thank MEC for a "Young Foreign Researchers" (SB2009-0186) contract and MINECO for "Juan de la Cierva" contract, respectively
This is the peer reviewed version of the following article: Sanjuán, A. M., Rashid, M. A., García-García, P., Martínez-Cuezva, A., Fernández-Rodríguez, M. A., Rodríguez, F. and Sanz, R. (2015), Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenes. Chem. Eur. J., 21: 3042–3052. doi: 10.1002/chem.201405789, which has been published in final form at 10.1002/chem.201405789. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
2015-12-10T12:48:00Z
2016-02-09T03:45:06Z
2015-02
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
0947-6539
http://hdl.handle.net/10259/3895
10.1002/chem.201405789
eng
Chemistry-A european journal. 2015. V. 21, n. 7, p. 3042-3052
http://dx.doi.org/10.1002/chem.201405789
info:eu-repo/grantAgreement/MINECO/CTQ2010-15358
info:eu-repo/grantAgreement/MINECO/CTQ2013-48937-C2-1-P
info:eu-repo/grantAgreement/MEC/SB2009-0186
info:eu-repo/grantAgreement/JCyL/BU237U13
info:eu-repo/semantics/openAccess
application/pdf
Wiley-VCH Verlag
https://riubu.ubu.es/bitstream/10259/3895/4/Sanjuan-CAEJ_2015.pdf.jpg
Hispana
TEXT
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RIUBU. Repositorio Institucional de la Universidad de Burgos
http://hdl.handle.net/10259/3895