Collect. Czech. Chem. Commun. 1992, 57, 525-530

An Alternative Synthesis of Ψ(CH2O) Pseudodipeptides

Jan Hlaváček and Vladimír Král

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


An alternative route to obtain Ψ(CH2O) pseudodipeptide unit based on insertion of carbens in hydroxylic bond of alcohols mediated by catalyst rhodium(II) acetate is described. In that way, N-protected derivatives of alaninol, valinol, isoleucinol leucinol and phenylalaninol were converted, upon a treatment with methyl or ethyl diazoacetate, to corresponding fully protected pseudodipeptides with methyleneoxy isostere bond which can be further used in peptide synthesis.