1238892-75-5Relevant academic research and scientific papers
Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes
Sanjun, Ana M.,Rashid, Muhammad A.,Garca-Garca, Patricia,Martnez-Cuezva, Alberto,Fernndez-Rodrguez, Manuel A.,Rodrguez, Flix,Sanz, Roberto
supporting information, p. 3042 - 3052 (2015/02/05)
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)-a-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.
Gold(I)-catalyzed enantioselective synthesis of functionalized indenes
Martinez, Alberto,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rodriguez, Felix,Sanz, Roberto
supporting information; experimental part, p. 4633 - 4637 (2010/08/22)
Chemical Equation Presented Can you dig it? An asymmetric synthesis of functionalized 1H-indenes from easily available ortho-(alkynyl)styrene derivatives under mild reaction conditions has been achieved. The reactions proceed through an unprecedented and selective 5-endo-dig gold(l)-catalyzed cycloisomerization or alkoxycyclization, if water or an alcohol is present (see scheme).
Halocyclization of o-(alkynyl)styrenes. Synthesis of 3-halo-1H-indenes
Sanz, Roberto,Martinez, Alberto,Garcia-Garcia, Patricia,Fernandez-Rodriguez, Manuel A.,Rashid, Muhammad A.,Rodriguez, Felix
supporting information; experimental part, p. 7427 - 7429 (2010/11/18)
o-(Alkynyl)styrenes undergo halocarbocyclization processes via a 5-endo-dig ring closure. By this strategy an efficient synthesis of 3-halo-1H-indene derivatives has been developed.
