Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams.
Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
Eiji
E
Yoneda
Shi-Wei
SW
Zhang
Da-Yang
DY
Zhou
Kiyotaka
K
Onitsuka
Shigetoshi
S
Takahashi
D000438:Alcohols / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D007769:Lactams / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D000438:Alcohols; D000466:Alkadienes; D000588:Amines; D007769:Lactams; D007783:Lactones; D009942:Organometallic Compounds; C025947:propadiene; D012428:Ruthenium