Practical ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine leading to alpha,beta-unsaturated lactones: concise stereoselective synthesis of (+)-isomintlactone.
We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of (+)-isomintlactone by the cyclocarbonylation of allenyl alcohol using 2,4,6-collidine.
Tsubuki
Masayoshi
M
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. tsubuki@hoshi.ac.jp
Takahashi
Kazunori
K
Honda
Toshio
T
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003511:Cyclohexanols / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D000466:Alkadienes; D003511:Cyclohexanols; D007783:Lactones; D011725:Pyridines; D013729:Terpenes; C025947:propadiene; C007106:gamma-collidine; D012428:Ruthenium; C409815:mintlactone