RT info:eu-repo/semantics/article
T1 Gold(I)-Catalyzed Cycloisomerizations and Alkoxycyclizations of ortho-(Alkynyl)styrenes
A1 Sanjuán Cortázar, Ana María
A1 Rashid, Muhammad A.
A1 García García, Patricia
A1 Martínez Cuezva, Alberto
A1 Fernández Rodríguez, Manuel A.
A1 Rodríguez, Félix
A1 Sanz Díez, Roberto
K1 asymmetric catalysis
K1 cyclization
K1 cycloisomerization
K1 gold
K1 indenes
K1 Química orgánica
K1 Chemistry, Organic
AB 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
PB Wiley-VCH Verlag
SN 0947-6539
YR 2015
FD 2015-02
LK http://hdl.handle.net/10259/3895
UL http://hdl.handle.net/10259/3895
LA eng
NO 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
DS Repositorio Institucional de la Universidad de Burgos
RD 25-nov-2024