Categories: C-O Bond Formation > Synthesis of alcohols (hydroxylation) >
Synthesis of hydroxy ketones and related compounds
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Various α-tosyloxyketones were efficiently prepared in high yields from the
reaction of ketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in
the presence of a catalytic amount of iodobenzene.
Y. Yamamoto, H. Togo, Synlett,
2006, 798-800.
α-Tosyloxyketones and α-tosyloxyaldehydes were directly prepared
from alcohols by treatment with iodosylbenzene and p-toluenesulfonic
acid monohydrate in good yields. Modified methods gave thiazoles, imidazoles
and imidazo[1,2-a]pyridines from alcohols in good to moderate yields.
M. Ueno, T. Nabana, H. Togo, J. Org. Chem., 2003, 68,
6424-6426.
α-Acetoxylation of ketones catalyzed by iodobenzene using^acetic anhydride and
30% aqueous hydrogen peroxide as the oxidant is an effective and economical
method for the preparation of α-acetoxy ketones in good yields.
J. Sheng, Y. Li, M. Tang, B. Gao, G. Huang, Synthesis, 2007,
1165-1168.
Bench stable N-Methyl-O-alkoxyformate hydroxylamine
hydrochloride reagents can be prepared in two high-yielding steps from N-Boc-N-methyl
hydroxylamine. Subsequent reaction with various carbonyl compounds give the
corresponding α-functionalised products in good yield via a proposed
[3,3]-sigmatropic rearrangement.
A. Hall, K. L. Jones, T. C. Jones, N. M. Killeen, R. Pörzig, P. H. Taylor, S.
C. Yau, N. C. O. Tomkinson, Synlett, 2006,
3435-3438.
The α-hydroxylation of α-alkynyl carbonyl compounds using IBX (o-iodoxybenzoic acid) gave various tertiary alcohols without dehydrogenation products under mildly acidic conditions.
S. F. Kirsch, J. Org. Chem., 2005,
70, 10210-10212.
S. F. Kirsch, J. Org. Chem., 2005,
70, 10210-10212.
Mn(OAc)3 based regioselective oxidation of various
2-cyclopentenone, 2-cyclohexenone and aromatic ketone derivatives in benzene
afforded the corresponding tertiary α'-acetoxy oxidation products in
good yields.
C. Tanyeli, C. Iyiguen, Tetrahedron, 2003, 59,
7135-7139.
A new mild RuO4-catalyzed ketohydroxylation of olefins is
reported. α-Hydroxy ketones were obtained with high regioselectivity
and in good to excellent yields.
B. Plietker, J. Org. Chem., 2003, 68, 7123-7125.
The reaction of alkenyl trichloromethyl carbinols with various nucleophiles
under protic basic conditions reveals that mercaptans participate by
α-substitution (SN2), wheareas hydroxide prefers γ-substitution
with stereoselective allylic transposition (SN2').
Regioselectivity with alkoxides depends upon alkene substitution.
J. L. Shamshina, T. S. Snowden, Org. Lett., 2006,
8, 5881-5884.
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