74753-00-7Relevant academic research and scientific papers
Hydrocarbonylating Cyclization of Dienes, 5. - Model Experiments for the Synthesis of the Acorane Skeleton from Substituted 1,4-Dienes
Eilbracht, Peter,Acker, Michael,Rosenstock, Bernd
, p. 151 - 158 (2007/10/02)
Heading towards the generation of the five-membered ring substitution pattern in the acorane skeleton (1) the hydrocarbonylating cyclization of various substituted 1,4-dienes 3 to cyclopentanones 4 and 5 was studied.While octacarbonyldicobalt as catalyst precurser nearly exclusively leads to linking of the less substituted carbon centers, the more active (cyclooctadiene)rhodium complex also effects the formation of new quaternary centers.The 1,5-dienes 15a-e converted under the same conditions revealed no tendency to isomerize to 1,4-dienes with the same carbon skeleton or to form analogous cyclization products.Finally, using the model substrate 3i the regio- and stereoselective synthesis of the cyclopentanone system 4i containing the same substitution pattern as the five-membered ring of the target molecule 1 can be accomplished. - Keywords: Carbonylation of 1,4-dienes / Catalysis, cobalt / Catalysis, rhodium / Cyclopentanone derivatives
