MOM-OR, MOM ether
T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 27-33, 708-711.
|H2O:||pH < 1, 100°C||pH = 1, RT||pH = 4, RT||pH = 9, RT||pH = 12, RT||pH > 12, 100°C|
|Reduction:||H2 / Ni||H2 / Rh||Zn / HCl||Na / NH3||LiAlH4||NaBH4|
|Oxidation:||KMnO4||OsO4||CrO3 / Py||RCOOOH||I2, Br2, Cl2||MnO2 / CH2Cl2|
0.01 mol-% Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield in 1 - 4 h. The solutions of haloalkyl ethers can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess carcinogenic haloalkyl ether is destroyed on workup.
M. A. Berliner, K. Belecki, J. Org. Chem., 2005, 70, 9618-9621.
Different types of unsymmetrically protected diols are available from the methylene acetal in a one-pot procedure. Monoprotected 1,2-diols with a silyl group at the less hindered hydroxy group as well as with a MOM group at the more hindered can be isolated in good yields. The reaction conditions are mild without affecting other functional groups.
H. Fujioka, K. Senami, O. Kubo, K. Yahata, Y. Minamitsuji, T. Maegawa, Org. Lett., 2009, 11, 5138-5141.
A simple and efficient method has been developed for chemoselective deprotection of phenolic methoxymethyl (MOM) ethers at room temperature using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst.
C. Ramesh, N. Ravindranath, B. Das, J. Org. Chem., 2003, 68, 7101-7103.
Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal-protected R-hydroxy ketones. Typically, high diastereomeric ratios and yields can be achieved for the synthesis of 1,2-anti-diols.
N. Bajwa, M. P. Jennings, J. Org. Chem., 2008, 73, 3638-3641.