Oxidative Cyclization of β-Hydroxyenones with Palladium(II): A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones
摘要:
A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.
Oxidative Cyclization of β-Hydroxyenones with Palladium(II): A Novel Entry to 2,3-Dihydro-4<i>H</i>-pyran-4-ones
作者:Maud Reiter、Sandrine Ropp、Véronique Gouverneur
DOI:10.1021/ol0361296
日期:2004.1.1
A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding beta-hydroxyenones. Attractive features of this transformation include the ready availability of the starting enones, the regiocontrol, and the easy access of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure enone.
Intramolecular Hetero-Michael Addition of β-Hydroxyenones for the Preparation of Highly Substituted Tetrahydropyranones
作者:Maud Reiter、Hazel Turner、Véronique Gouverneur
DOI:10.1002/chem.200600415
日期:2006.9.18
6-endo-trig ring closure to form highly substituted tetrahydropyranones. Amberlyst-15, Al(ClO(4))(3) x 9 H(2)O and [Pd(MeCN)(4)](BF(4))(2) were found to be suitable catalysts for these intramolecular conjugate additions, preventing side reactions, such as dehydration or retroaldolisation. The use of [Pd(MeCN)(4)](BF(4))(2) is particularly effective, as this palladium-mediated reaction is under kinetic control