Categories: C=O Bond Formation > Synthesis of ketones
Synthesis of α-hydroxy ketones and aldehydes
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Various terminal olefinic compounds are directly
converted into the corresponding α-hydroxy ketones in good yields by potassium
permanganate oxidation. The reaction is highly chemoselective in the
presence of differently protected hydroxy groups.
C. Bonini, L. Chiummiento, M. Funicello, P. Lupattelli, M. Pullez, Eur. J. Org. Chem., 2006,
80-83.
A direct, mild ketohydroxylation of various 1-aryl-1-alkenes with H2O2,
catalyzed by the inexpensive 12-tungstophosphoric acid/cetylpyridinium
chloride system, gave acyloins in good yields and high regioselectivies.
Y. Zhang, Z. Shen, J. Tang, Y. Zhang, L. Kong, Y. Zhang, Org. Biomol. Chem., 2006, 4, 1478-1482.
A highly enantioselective method for catalytic reductive coupling of alkynes
and aldehydes afforded allylic alcohols with complete E/Z selectivity,
generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with
ozonolysis, this process allows the enantioselective synthesis of α-hydroxy
ketones.
K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443.
IBX has been utilized for the oxidation of various epoxides and aziridines as
their β-cyclodextrin complexes in water to afford α-hydroxyketones and α-aminoketones
in good yields, respectively.
K. Surendra, N. S. Krishnaveni, M. A. Reddy, Y. V. D. Nageswar, K. R. Rao, J.
Org. Chem., 2003, 68, 9119-9121.
A mild and efficient oxidation of alcohols with o-iodoxybenzoic acid
(IBX) is catalyzed by β-cyclodextrin in a water/acetone mixture (86:14).
Various alcohols were oxidized at room temperature in
excellent yields.
K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar, K.
Rama Rao, J. Org. Chem., 2003,
68, 2058-2059.
A two-step sequence of asymmetric dihydroxylation and regioselective
monooxidation gave enantiopure α-hydroxy ketones (acyloins). The
combination of RuCl3/Oxone/NaHCO3 was used in the
first catalytic regioselective oxidation of vic-diols to α-ketols.
B. Plietker, Org. Lett., 2004, 6, 289-291.
A catalyst comprising of Ph3PAuCl and AgSbF6 efficiently
hydrolyzes terminal alkyne groups of propargyl acetates in the absence of acid
promoters at ambient temperature within a short time. Effective regioselective
hydration is facilitated by the neighboring carbonyl group. Synthesis of
actinopolymorphol B is achieved involving hydration of the propargyl acetate as
the key step.
N. Ghosh, S. Nayak, A. K. Sahoo, J. Org. Chem., 2011,
76, 500-511.
Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy
ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2)
as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl
functional groups are tolerated during the methanolysis and acetonidation of the
functionalized epoxides.
K. Jeyakumar, D. K. Chand, Synthesis, 2008,
807-819.
Grubbs' 2nd generation metathesis catalyst can be used in tandem olefin
metathesis/oxidation protocols. These ruthenium-catalyzed processes provide
access to cis-diols or α-hydroxy ketones from simple olefinic starting
materials.
A. A. Scholte, M. H. An, M. L. Snapper, Org. Lett.,
2006, 8, 4759-4762.
