Journal of Organic Chemistry p. 4984 - 4993 (1987)
Update date:2022-08-30
Topics:
Dangles, O.
Guibe, F.
Balavoine, G.
Lavielle, S.
Marquet, A.
N-Allyloxycarbonyl (Alloc) derivatives of amines and amino acids are quantitatively and very rapidly converted to free amino compounds by palladium-catalyzed hydrostannolytic cleavage with tributyltin hydride in the presence of a proton donor (acetic acid, p-nitrophenol, pyridinium acetate, water).A similar procedure can be used for the deprotection of allyl (All) carboxylates and allyl aryl ethers.Deprotection experiments were performed on various mixed N-Alloc and O-Bzl, N-Z and O-All, N-Alloc and O-t-Bu, and N-alloc- and N-Boc-protected amino acid derivatives.The palladium-catalyzed hydrostannolytic cleavage is fully compatible with the Bzl and Z protecting groups; furthermore the BOC and t-Bu groups and the Alloc and All groups appear to be ortogonal.The reliability of the Alloc methodology for temporary protection of the α-amino functions is ilustrated by the solid-phase synthesis of the biologically active undecapeptide substance P.
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