1398121-10-2Relevant 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.
Straightforward synthesis of dihydrobenzo[a]fluorenes through Au(I)- catalyzed formal [3 + 3] cycloadditions
Garcia-Garcia, Patricia,Rashid, Muhammad A.,Sanju-An, Ana M.,Fernandez-Rodriguez, Manuel A.,Sanz, Roberto
, p. 4778 - 4781,4 (2012/12/12)
Dihydrobenzo[a]fluorene derivatives have been prepared by a formal intramolecular [3 + 3] cycloaddition of o-alkynylstyrenes bearing a secondary alkyl group at the β-position of the styrene moiety. The process, catalyzed by a cationic gold(I) complex, involves a 1,2-hydride migration as the key step. 6,11-Dihydro-5H-benzo[a]fluorenes could be obtained from the initially generated 6,6a-dihydro-5H-benzo[a]fluorenes by subsequent heating of the reaction mixture under gold(I) or Bronsted acid catalysis or directly by conducting the reactions at high temperature.
Straightforward synthesis of dihydrobenzo[a]fluorenes through Au(I)- catalyzed formal [3 + 3] cycloadditions
García-García, Patricia,Rashid, Muhammad A.,Sanju-An, Ana M.,Fernández-Rodríguez, Manuel A.,Sanz, Roberto
, p. 4778 - 4781 (2013/01/15)
Dihydrobenzo[a]fluorene derivatives have been prepared by a formal intramolecular [3 + 3] cycloaddition of o-alkynylstyrenes bearing a secondary alkyl group at the β-position of the styrene moiety. The process, catalyzed by a cationic gold(I) complex, inv
