Ontology highlight
ABSTRACT:
SUBMITTER: Horino Y
PROVIDER: S-EPMC2880645 | biostudies-literature | 2009 Mar
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20090301 8
The gold(I)-catalyzed cycloisomerization of 1,5-enynes and 1,4-allylallenes to tetracyclododecane and tetracyclotridecane derivatives, respectively, is reported. Complexation of the cationic gold(I) complex to either the alkyne or allene moiety induces an intramolecular addition of the alkene, leading to a gold(I)-stabilized carbenoid intermediate. This intermediate undergoes a formal sp(3) C-H insertion to generate the tetracyclic adduct. A series of deuterium labeling experiments showed that t ...[more]