451501-38-5Relevant academic research and scientific papers
A new method for the synthesis of cycloheptenones by RhI-catalyzed intramolecular hydroacylation of 4,6-dienals
Sato, Yoshihiro,Oonishi, Yoshihiro,Mori, Miwako
, p. 1218 - 1221 (2002)
The size of the ring formed in the Rh1-catalyzed intramolecular hydroacylation of 4,6-dienals is dependent on the presence of a substituent at C7 and the geometry of the olefin. Cyclization of 4,6-dienals with a substituent at the C7 position (1; R1 = alkyl, R2 = H) produced cycloheptenones (2) as the major product (see scheme), while that of 4,6-dienals with no substituent at the terminus of the diene (1; R1 = H) preferentially gave cyclopentanones. The cyclization of substrates containing a 6E olefin produced cycloheptenones as the major product, while a cyclopentanone was obtained from a substrate having a 6Z olefin. dppe = 1,2-bis(diphenylphosphanyl) ethane.
Rh(I)-catalyzed intramolecular hydroacylation in ionic liquids
Oonishi, Yoshihiro,Ogura, Jiro,Sato, Yoshihiro
, p. 7505 - 7507 (2008/03/14)
Rh(I)-catalyzed hydroacylation of 4-alkenal or 4,6-dienal using ionic liquids (ILs) as reaction media proceeded smoothly, giving cyclopentanone or cycloheptenone derivatives in good yields. It was found that the IL recovered after the reaction, which shou
Rhodium(I)-catalyzed intramolecular hydroacylation of 4,6-dienals: Novel synthesis of cycloheptenones
Oonishi, Yoshihiro,Mori, Miwako,Sato, Yoshihiro
, p. 2323 - 2336 (2008/02/13)
Rhodium(I)-catalyzed hydroacylation of 4,6-dienals was investigated. Hydroacylation of 4,6-dienals with a substituent at the C7 position produced cycloheptenone derivatives as the major products, while the cyclization of 4,6-dienals with no substituent at the terminus of the diene moiety preferentially gave cyclopentanone derivatives. The olefinic geometry of the diene moiety in 4,6-dienals also affected the reaction course, and the cyclization of substrates with an E-olefin at the C6 position produced cycloheptenone derivatives as the major products, while a cyclopentanone derivative was obtained from a substrate with a Z-olefin at the C6 position. Georg Thieme Verlag Stuttgart.
