Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes.
Treatment of cyclic beta-keto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)(3)(thf)](2), gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.
Kuninobu
Yoichiro
Y
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan. kuninobu@cc.okayama-u.ac.jp
Morita
Junya
J
Nishi
Mitsumi
M
Kawata
Atsushi
A
Takai
Kazuhiko
K
D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012211:Rhenium / Q000737:chemistry*
D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D004952:Esters; D000644:Quaternary Ammonium Compounds; C458301:bicyclo(3.3.1)nonane; D012211:Rhenium; C009405:tetrabutylammonium