184089-72-3Relevant academic research and scientific papers
Diastereoselective iodocarbocyclization reaction of 2- or 3-oxy-4-pentenylmalonate derivatives
Inoue, Tadashi,Kitagawa, Osamu,Oda, Yoko,Taguchi, Takeo
, p. 8256 - 8263 (2007/10/03)
1,2- Or 1,3-asymmetric induction in the iodocarbocyclization reaction of 4-pentenylmalonate derivatives having a stereogenic center at an allylic or a homoallylic position has been investigated. The iodocarbocyclization reactions of 3-oxy-4-pentenylmalonate derivatives proceeded with high cis-selectivity through stereoelectronic control of the oxygenated substituent at an allylic position. In the reaction of (S)-2-siloxy-4-pentenylmalonate, an excellent diastereoselectivity was achieved through the utilization of double stereodifferentiation with a chiral titanium catalyst. Furthermore, as an application of the present reaction, the asymmetric syntheses of cyclosarkomycin and a synthetic intermediate of brefeldin A from optically pure 2- and 3-oxy-4-pentenylmalonate derivatives are also described.
