Synthesis of 1,3-diketones
In oxidation of β-hydroxyketones to β-diketones, o-iodoxybenzoic acid (IBX) was found to be efficient, operationally easy, and superior to other common oxidants. The reaction is suitable for milligram- to gram-scale oxidations.
S. L. Bartlett, C. M. Beaudry, J. Org. Chem., 2011, 76, 9852-9855.
An efficient one-pot transformation of β-hydroxycarbonyl compounds to α-brominated 1,3-dicarbonyl compounds is achieved with MoO2Cl2 in the presence of N-bromosuccinimide. All the reactions were carried out under mild conditions and provide good yields. No bromination occurs at benzylic and allylic positions.
K. Jeyakumar, D. K. Chand, Synthesis, 2009, 306-310.
An unprecedented asymmetric aza-Claisen rearrangement between enantioenriched α-chiral allylamines and allenones provides - followed by hydrolysis - structurally diverse δ-chiral β-diketones in good to excellent yields with excellent retention of enantiopurity. This protocol enabled the construction of an all-carbon quaternary stereocenter with high enantiopurity.
R.-H. Dai, Q. Wang, Z.-X. Chen, S.-K. Tian, J. Org. Chem., 2021, 86, 3065-3073.
An oxidative coupling method for alkyne difunctionalization under metal-catalyst-free conditions affords various β-ketodithianes in very good yields with high regioselectivities. The reaction provides valuable dithianes with controlled formation of a new C-C bond and a C-O bond via a radical coupling pathway.
J. Lai, L. Tian, X. Huo, Y. Zhang, X. Xie, S. Tang, J. Org. Chem., 2015, 80, 5894-5899.