Tandem enyne metathesis-Diels-Alder reaction for construction of natural product frameworks.
Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels-Alder process. Some domino RCM-Diels-Alder reactions are performed, suggesting a possible beneficial effect of the ruthenium catalyst in the cycloaddition process. Other examples require Lewis acid cocatalyst. When applied to aromatic ynamines or enamines, a new synthesis of vinylindoles is achieved. Monitorization of several metathesis reactions with NMR shows the different behavior for ruthenium catalysts. New carbenic species are detected in some reactions with an important dependence on the solvent used.
Rosillo
Marta
M
Universidad San Pablo-CEU, Departamento de Química and Servicio de rayos-X, Facultad de Ciencias Experimentales y de la Salud, Urb. Montepríncipe, 28668 Boadilla del Monte (Madrid), Spain.
Domínguez
Gema
G
Casarrubios
Luis
L
Amador
Ulises
U
Pérez-Castells
Javier
J
D000466:Alkadienes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis*; D002384:Catalysis; D006838:Hydrocarbons; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000466:Alkadienes; D000480:Alkynes; D001685:Biological Factors; D006838:Hydrocarbons; D007211:Indoles; D012997:Solvents; D014753:Vinyl Compounds; C030011:carbene; D012428:Ruthenium; D008697:Methane