Deprotection by Palladium-Catalyzed Allyl Transfer

BM Trost. New rules of selectivity allyl alkylations catalyzed by palladium. Acc Chem Res 13, 385, 1980. 

H Kuntz, C Unverzagt. The allyloxycarbonyl (Aloe) moiety — conversion of an unsuitable into a valuable amino protecting group for peptide synthesis. Angew Chem Int Edn Engl 23, 436, 1984. 

FIGURE 3.13 Cleavage of an allyl-based protector (Stevens Watanabe, 1950) by palladium-catalyzed allyl transfer to a nucleophile in the presence of a proton donor.27-28 

O Dangles, F Guibe, G Balavoine, S Lavielle. A Marquet. Selective cleavage of the allyl and allyloxycarbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application of the selective protection-deprotection of amino acid derivatives and in peptide synthesis. J Org Chem 52, 4984, 1987. 

A Loffet, HX Zhang. Allyl-based groups for side-chain protection of amino-acids. Int J Pept Prot Res 42, 346, 1993. 

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