Summary.
Homochiral Nα-methyl-2,3-diaminopropionic and Nα-methyl-2,4-diaminobutyric acid derivatives 8a,b were obtained via a stereoconservative four-step synthesis starting from hexafluoroacetone protected L-aspartic and L-glutamic acid 2a,b, respectively. Hexafluoroacetone protected ω-isocyanato-α-methylamino acids 4a,b– the key intermediates of the synthesis – are versatile building blocks for amino acid and peptide modification and promising candidates for combinatorial chemistry. Upon reaction with alcohols, compounds 4 give activated N ω-urethane protected ω-amino-α-methylamino acid derivatives 5–7; upon reaction with amines, ω-ureido-α-methylamino acid derivatives 10–12 and 3-methylamino-pyrrolidin-2-ones 13 are available.
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Received November 17, 1999. Accepted November 26, 1999
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Burger, K., Spengler, J., Hennig, L. et al. Synthesis of Derivatives of ω-Isocyanato-α-methylamino, ω-Ureido-α-methylamino, and Nα-Methyl-α, ω-diamino Acids. Monatshefte für Chemie 131, 463–473 (2000). https://doi.org/10.1007/PL00010315
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DOI: https://doi.org/10.1007/PL00010315