Monatshefte fur Chemie p. 463 - 473 (2000)
Update date:2022-07-31
Topics:
Burger, Klaus
Spengler, Jan
Hennig, Lothar
Herzschuh, Rainer
Essawy, Samy A.
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 Nω-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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Doi:10.1007/BF00903044
(1950)Doi:10.1021/jo991625m
(2000)Doi:10.1021/ja992365t
(1999)Doi:10.1039/a902662b
(1999)Doi:10.1007/s10600-021-03337-7
(2021)Doi:10.1016/j.bmc.2004.01.002
(2004)