Categories: C-O Bond Formation > Synthesis of alcohols (hydroxylation) >
Synthesis of β-hydroxy ketones, esters, nitriles and related compounds
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Recent Literature
The direct addition of water and a variety of alcohols to activated olefins
was observed in the presence of nucleophilic phosphine catalysts. Unlike
existing methods, the reactions proceed at room temperature and in the absence
of transition metals, or strong acids or bases.
I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc., 2003,
125, 8696-8697.
A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot
reaction sequence using commercially available catalysts at low catalyst
loadings gives β-hydroxy and β-amino esters in high yield and excellent
enantiopurity. The generation of quaternary stereocenters and application in
gram-scale synthesis were also realized, with no requirements of inert or
anhydrous reaction conditions.
H. Jiang, B. Gschwend, Ł. Albrecht, K. A. Jørgensen, Org. Lett., 2010,
12, 5052-5055.
An efficient intermolecular conjugate addition of various primary and secondary
alcohols to unsaturated ketones and esters is catalyzed by the free carbene
derived from IMes·HCl. No oligomerization is observed under these mild
conditions. In addition to reactions with activated alkenes, IMes catalyzes the
formation of vinyl ethers through the 1,4-addition of alcohols to ynones.
E. M. Phillips, M. Riedrich, K. A. Scheidt, J. Am. Chem. Soc., 2010,
132, 13179-13181.
A new palladium-catalyzed method allows the oxygenation of unactivated sp3
C-H bonds of a wide variety of alkane substrates containing readily
available oxime and/or pyridine directing groups with extremely high levels
of chemo-, regio-, and in some cases diastereoselectivity.
L. V. Desai, K. L . Hull, M. S. Sanford, J. Am. Chem. Soc.,
2004,
126, 9542-9543.
R. Shintani, K. Okamoto, T. Hayashi, Org. Lett.,
2005,
7, 4757-4759.
