Atom-efficient assembly of 1,5-oxygen-bridged medium-sized carbocycles by sequential combination of a Ru-catalyzed alkyne-alkene coupling and a Prins-type cyclization.
Ruthenium-catalyzed coupling of readily accessible 1-trimethylsilyl-1-alkyn-3-ols to allyl ethyl ether followed by in situ ketalization and Lewis-acid induced cyclization affords 1,5-oxygen-bridged eight- and nine-membered carbocycles, products which are difficult to construct with previously published strategies.
López
Fernando
F
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Castedo
Luis
L
Mascareñas
José L
JL
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; D012428:Ruthenium