Regioselective and sequential reactivity of activated 2,5-diketopiperazines

Daniel Farran (1) , Delphine Echalier (1) , Jean Martinez (1) , Georges Dewynter (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

The electrophilic reactivity of Boc-DKPs has been studied. Thanks to Boc activation, the opening ability of carbonyl lactam groups is enhanced. According to experimental conditions, this enabled the synthesis of Boc-amino acid derivatives or original dipeptides via a regioselective and sequential way.

Mots clés: diketopiperazines; lactam activation; Boc group; electrophilic reactivity amino acid

Domaines: Chimie organique

Daniel Farran, Delphine Echalier, Jean Martinez, Georges Dewynter. Regioselective and sequential reactivity of activated 2,5-diketopiperazines. Journal of Peptide Science, 2009, 15, pp.474-478. ⟨10.1002/psc.1139⟩. ⟨hal-00390590⟩