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Título : Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenes
Autor : Sanjuán Cortázar, Ana María
Rashid, Muhammad A.
García García, Patricia
Martínez Cuezva, Alberto
Fernández Rodríguez, Manuel A.
Rodríguez, Félix
Sanz Díez, Roberto
Publicado en: Chemistry-A european journal. 2015. V. 21, n. 7, p. 3042-3052
Editorial : Wiley-VCH Verlag
Fecha de publicación : feb-2015
ISSN : 0947-6539
DOI: 10.1002/chem.201405789
Resumen : 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
Palabras clave: asymmetric catalysis
cyclization
cycloisomerization
gold
indenes
Materia: Química orgánica
Chemistry, Organic
URI : http://hdl.handle.net/10259/3895
Versión del editor: http://dx.doi.org/10.1002/chem.201405789
Aparece en las colecciones: Artículos SINTORG

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