Keywords. Hexafluoroacetone; ω-Isocyanato-α-methylamino acid derivatives; Nα-Methyl-2,3-diaminopropionic acid derivatives and homologues; ω-Ureido-α-methylamino acids; 3-Methylamino-pyrrolidin-2-ones.
Springer Online Journal Archives 1860-2000
Chemistry and Pharmacology
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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