Osmium tetroxide
Name Reactions
Recent Literature
Resin-OsO4 are very efficient catalysts for the dihydroxylation
of various olefins to afford vicinal diols with high yields irrespective of
the cooxidant used. Resin-OsO4 is recovered quantitatively by a
simple filtration and reused for a number of cycles with consistent
activity. The high binding ability of the heterogeneous osmium catalysts
enables the use of an equimolar ratio of a chiral ligand such as (DHQD)2PHAL
to osmium to give excellent enantioselectives in the asymmetric
dihydroxylation.
B. M. Choudary, N. S. Chodari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc.,
2002, 124, 5341-5349.
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.
S. V. Ley, C. Ramarao, A.-L. Lee, N. Ostergaard, S. C. Smith, I. M.
Shirley, Org. Lett., 2003, 5, 185-187.
The cis-dihydroxylation of olefin-containing potassium alkyl- and
aryltrifluoroborates proceeds readily in moderate to excellent yields. The
resulting diols are efficient coupling partners in Suzuki-Miyaura-type
reactions with both alkenyl and aryl bromides.
G. A. Molander, R. Figueroa, Org. Lett.,
2006, 8, 75-78.
The OsO4-catalyzed direct oxidation of olefins via the
carbon-carbon cleavage of an osmate ester by the action of oxone allows the
preparation of ketones or carboxylic acids in high yields. This method
should be applicable as an alternative to ozonolysis.
B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc., 2002,
124, 3824-3825.
B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc., 2002,
124, 3824-3825.
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.