Synthesis of β,β′-diamino acids from α-amino acid-derived β-lactams by ring opening with nucleophiles. Utilization in the synthesis of peptidomimetics
2008; Elsevier BV; Volume: 64; Issue: 37 Linguagem: Inglês
10.1016/j.tet.2008.07.006
ISSN1464-5416
AutoresAlexander A. Taubinger, Dieter Fenske, Joachim Podlech,
Tópico(s)Synthesis and Catalytic Reactions
ResumoRing opening of protected 3-aminoalkyl-substituted azetidin-2-ones with O-, N- or S-nucleophiles led to β,β′-diaminocarboxylic esters, amides and thioesters, respectively. The reaction outcome is improved by the addition of catalytic amounts of sodium azide. Utilization of a glycine derivative with unprotected amino function as nucleophile was possible. When bulkier amino acid esters were used, the intermediate acid azide underwent a Curtius rearrangement. The isocynates formed were trapped as the corresponding urea derivatives. Reduction of β-lactam's amide moiety led to diaminoalcohols.
Referência(s)