Categories: C=O Bond Formation > Synthesis of Ketones
Synthesis of 1,3-diketones
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Recent Literature
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.
Related
In situ generated hypoiodite catalyzes an oxidative rearrangement of
chalcones under mild and metal-free conditions. This environmental-benign
protocol avoids the use of rare or toxic metals.
M. Zheng, C. Huang, J.-Z. Yan, S.-L. Xie, S.-J. Ke, H.-D. Xia, Y.-N. Duan, J. Org. Chem., 2023, 88,
1504-1514.
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.