Sodium periodate
Recent Literature
Osmium tetroxide has been microencapsulated in a polyurea matrix. These
microcapsules have been effectively used as recyclable catalysts in the
dihydroxylation and the oxidative cleavage of olefins.
S. V. Ley, C. Ramarao, A.-L. Lee, N. Ostergaard, S. C. Smith, I. M.
Shirley, Org. Lett., 2003, 5, 185-187.
Specific oxidation protocols have been developed for the cleavage of styrenes,
aliphatic olefins, and terminal aliphatic olefins to carbonyl compounds with
ruthenium trichloride as catalyst. Olefins that are not fully substituted are
converted to aldehydes rather than carboxylic acids.
D. Yang, C. Zhang, J. Org. Chem., 2001, 66,
4814-4818.
A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and
3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the
synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such
as piperazine, morpholine, and 1,4-diazepane annulated β-lactam derivatives.
W. Van Brabandt, M. Vanwalleghem, M. D'hooghe, N. De Kimpe, J. Org. Chem., 2006,
71, 7083-7086.
An improved protocol for the RuO4-catalyzed syn-dihydroxylation
uses only 0.5 mol% catalyst under acidic conditions. Various olefins can be
hydroxylated in good to excellent yields with only minor formation of side
products.
B. Plietker, M. Niggemann, Org. Lett., 2003, 3353-3356.
LiBr is an efficient catalyst for the dihydroxylation of alkenes to afford
either syn or anti diols with excellent diastereoselectivity
depending upon the use of NaIO4 or PhI(OAc)2 as the
oxidants.
L. Emmanuvel, T. M. A. Shaikh, A. Sudalai, Org. Lett.,
2005,
7, 5071-5074.
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.
A new, one-pot method is described for the removal of O- and N-allyl
protecting groups under oxidative conditions at near neutral pH. The
allyl group undergoes hydroxylation and subsequent periodate scission of
the vicinal diol. Repetition of this reaction sequence on the enole
tautomer of the aldehyde intermediate releases the deprotected
functional group.
P. I. Kitov, D. R. Bundle, Org. Lett., 2004, 3,
2835-2838.
A catalytic, asymmetric conjugate addition of carbamates to enoyl systems provides a highly enantioselective two-step
access to N-protected β-amino acids.
C. Palomo, M. Oiarbide, R. Halder, M. Kelso, E. Gómez-Bengoa, J. García, J. Am. Chem. Soc.,
2004,
126, 9188-9189.
A highly
enantioselective and catalytic vinylation of aldehydes leads to allylic alcohols
that are then transformed to the allylic amines via Overman's [3,3]-sigmatropic
rearrangement of imidates. Oxidative cleavage of the allylic amines furnishes amino acids in good yields and excellent ee's. The scope and utility of this
method are demonstrated by the synthesis of challenging allylic amines and their
subsequent transformation to valuable nonproteinogenic amino acids, including
both D and L configured (1-adamantyl)glycine.
Y. K. Chen. A. E. Lurain, P. J. Walsh, J. Am. Chem. Soc., 2002,
124, 12225-12231.
Deactivated arenes were mono- or diiodinated with strong electrophilic I+
reagents, which were prepared from NaIO4 and either I2
or KI in concentrated sulfuric acid, using either a ‘direct’ or an ‘inverse’
method of aromatic iodination to give mono- or diiodinated pure products in
good yields.
L. Kraszkiewicz, M. Sosnowski, L. Skulski,
Synthesis, 2006, 1195-1199.
A novel, high-yielding method for sulfation of alcohols proceeds via
sulfite- and sulfate diester intermediates. Sulfite diesters serve as
versatile sulfate monoester precursors, that allow interesting
transformations.
M. Huibers, I. Manuzi, F. P. J. T. Rutjes, F. L. van Delft, J. Org. Chem., 2006,
71, 7473-7476.
Arylboronic acids and aryl trifluoroborates are synthesized in a one-pot
sequence by Ir-catalyzed borylation of arenes. To prepare the arylboronic acids,
the Ir-catalyzed borylation is followed by oxidative cleavage of the pinacol
boronates with NaIO4. To prepare the aryltrifluoroborate, the
Ir-catalyzed borylation is followed by displacement of pinacol by KHF2.
J. M. Murphy, C. C. Tzschucke, J. F. Hartwig, Org. Lett., 2007,
9, 757-760.
