Categories: O-H Bond Formation >
Cleavage of esters
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Recent Literature
Acetyl-, benzoyl- and pivoyl-protected alcohols and phenols undergo smooth
deacylation in a two-phase system of powdered NaOH and Bu4NHSO4
in THF or CH2Cl2.
R. D. Crouch, J. S. Burger, K. A. Zietek, A. B. Cadwallader, J. E. Bedison,
M. M. Smielewska, Synlett, 2003, 991-992.
The reaction of different esters, thioesters and amides derived from pivalic,
benzoic and 4-tert-butylbenzoic acids with an excess of lithium and a
catalytic amount of naphthalene led, after methanolysis, to the
corresponding alcohols, thiols and amines, respectively, through a reductive
non-hydrolytic procedure.
C. Behloul, D. Guijarro, M. Yus, Synthesis, 2006, 309-314.
Deprotection of allyl ethers, amines and esters to
liberate hydroxyl, amino and acid groups is achieved under mild conditions. The
reagent combination employed for this transformation is polymethylhydrosiloxane
(PMHS), ZnCl2 and Pd(PPh3)4.
S. Chandrasekhar, R. Reddy, R. J. Rao, Tetrahedron, 2001, 57,
3435-3438.
The homoallyl moiety (hAllyl) can be used as a general protecting group for
several functionalities. It can be chemoselectively removed via a sequential,
one-pot cross-metathesis/elimination sequence.
B. H. Lipshutz, S. Ghorai, W. W. Y. Leong, J. Org. Chem., 2009,
74, 2854-2857.
