Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams.J Org Chem. 2003 Oct 31; 68(22):8571-6.JO
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.