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 reaction of chiral 1-aminoalkylepoxides with CO2, generated from
acidic treatment of an aqueous solution of NaHCO3 at room temperature,
efficiently afforded enantiopure cyclic carbonates with total selectivity.
Carbonates were readily transformed into the corresponding diols by reaction
with LiAlH4 or by basic hydrolysis.
J. M. Concellón, V. del Solar, S. Carcía-Granda, M. R. Díaz, J. Org. Chem.,
2007,
72, 7567-7568.
