Categories: O-H Bond Formation >
Cleavage of acetals
Protecting Groups
Recent Literature
Acetals and ketals are readily deprotected under neutral conditions in the
presence of acetone and indium(III)
trifluoromethanesulfonate as catalyst at room temperature or mild microwave
heating conditions to give the corresponding aldehydes and ketones in good to
excellent yields.
B. T. Gregg, K. C. Golden, J. F. Quinn, J. Org. Chem., 2007,
72, 5890-5893.
Er(OTf)3 is an efficient Lewis acid catalyst in a mild
deprotection of benzylidene derivatives.
A. Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, G. Romeo, Org. Biomol. Chem., 2005, 3, 4129-4133.
A new and efficient method for the cleavage of the PMP, THP and 1,3-dithiane
protecting groups with Selectfluor™ has been developed.
J. Liu, C.-H. Wong, Tetrahedron Lett., 2002, 43,
4037-4039.
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.
The use of CeCl3·7H2O enables a highly selective cleavage of MEM
ethers in high yields in refluxing acetonitrile under mild and neutral reaction
conditions. The reaction tolerates other hydroxyl
protecting groups such as Bn, TBDPS, Ac, Me, Tr, PMB, benzylidene, THP, MOM, BOM,
and NHAc.
G. Sabitha, R. Satheesh Babu, M. Rajkumar, S. Srividya, J. S. Yadav,
Org. Lett., 2001, 3, 1149-1151.
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.
H. Fujioka, K. Senami, O. Kubo, K. Yahata, Y. Minamitsuji, T. Maegawa, Org. Lett., 2009,
11, 5138-5141.