Ruthenium-catalyzed [2 + 2] cycloaddition of allenynes leading to a bicyclo[4.2.0]octa-1(8),5-diene skeleton.
The reaction pathway of Cp*RuCl(cod)-catalyzed cyclization of allenynes was dramatically changed depending on the type of solvent employed. That is, while a cyclodimerization of allenyne proceeded to give a pentacyclic compound in toluene, a bicyclo[4.2.0]octa-1(8),5-diene derivative was exclusively produced by [2 + 2] cycloaddition of allenyne in methanol. It was also demonstrated that the [2 + 2] cycloaddition was catalyzed by a cationic ruthenium complex generated from Cp*RuCl(cod) and methanol in situ.
Saito
Nozomi
N
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. nozomi-s@pharm.hokudai.ac.jp
Tanaka
Yuki
Y
Sato
Yoshihiro
Y
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D000432:Methanol; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*
D001643:Bridged Bicyclo Compounds; D011090:Polyenes; D012428:Ruthenium; D000432:Methanol