106993-93-5Relevant academic research and scientific papers
Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
Molander, Gary A.,Camera, Kimberly O.
, p. 830 - 846 (2007/10/02)
Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.
1,5-DICARBONYL COMPOUNDS A GENERAL PREPARATION METHOD
Duhamel, P.,Hennequin, L.,Poirier, J. M.,Tavel, G.,Vottero, C.
, p. 4777 - 4786 (2007/10/02)
In this report, a general method for the preparation of 1,5-dicarbonyl compounds and six membered ring annelation is described.This method involves the reaction of hemiacetal vinylogs 1 with enol ethers 2 or 3 in the presence of a Lewis acid.This reaction was successfully applied to the enol ethers of α and α,α'-hindered ketones such as 2,2,6-trimethyl cyclohexanone. α-Cyperone and 6-epi-α-cyperone were obtained using this process.
UNE METHODE SIMPLE ET EFFICACE DE PREPARATION DE COMPOSES DICARBONYLES-1,5
Duhamel, Pierre,Hennequin, Laurent,Poirier, Nelly,Poirier, Jean-Marie
, p. 6201 - 6204 (2007/10/02)
We describe a convenient preparation method of 1,5-dicarbonyl compounds from enol ethers, methyl vinyl ketone and boron trifluoride etherate.In the presebce of an alcohol, high or quantitative yields are obtained even with enol ethers of hindered ketones.
