Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

ABSTRACT: A Rh(I)-catalyzed cyclocarbonylation reaction of allenol esters has been examined and its synthetic viability established for the conversion of trisubstituted allenes to bicyclo[4.3.0] and -[5.3.0] skeletons possessing an alpha-acetoxy cyclopentadienone. Tetrasubstituted allenol acetates gave elimination products, providing examples of a cyclocarbonylation reaction between an alkyne and a latent cumulene or cumulene equivalent. Cleavage of the acetate affords a free hydroxyl group illustrating the utility of this method for accessing alpha-hydroxy carbonyls from allenol esters.

SUBMITTER: Brummond KM 

PROVIDER: S-EPMC3433757 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature