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Development of Novel Cyclizations via Rhodacycle Intermediate and Its Application to Synthetic Organic Chemistry.
Oonishi, Yoshihiro.
Affiliation
  • Oonishi Y; Faculty of Pharmaceutical Sciences, Hokkaido University.
Chem Pharm Bull (Tokyo) ; 63(6): 397-407, 2015.
Article in En | MEDLINE | ID: mdl-26027463
Novel Rh(I)-catalyzed cyclizations through a different type of rhodacycle intermediate which is formed by hydroacylation of 4,6-dienal or oxidative addition of diene and alkene are described. Hydroacylation of 4,6-dienal afforded various 7-membered rings in good to high yields, while cycloisomerization of diene and alkene provided 5- or 6-membered rings in good yields. On the basis of these studies, we have also succeeded in developing the sequential reaction of hydroacylation followed by cycloisomerization to produce bicyclic compounds in a stereoselective manner and thus this reaction was expanded to the synthesis of epiglobulol. Furthermore, both Rh(I)-catalyzed hydroacylation and cycloisomerization using ionic liquid (IL) as a solvent were investigated and it was found that the IL recovered after the reaction, which contains the Rh(I) catalyst, could be recycled several times without loss of catalytic activity.
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Rhodium / Alkenes / Chemistry Techniques, Synthetic / Hydrocarbons, Cyclic Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2015 Document type: Article Country of publication: Japan

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Rhodium / Alkenes / Chemistry Techniques, Synthetic / Hydrocarbons, Cyclic Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2015 Document type: Article Country of publication: Japan