SYNTHESIS OF N-ALPHA, N-BETA-ALKYLATED DIAMINOPROPIONIC ACID ANALOGS

Authors
SOLOMON ME LYNCH CL RICH DH
Citation
Me. Solomon et al., SYNTHESIS OF N-ALPHA, N-BETA-ALKYLATED DIAMINOPROPIONIC ACID ANALOGS, Tetrahedron letters, 36(28), 1995, pp. 4955-4958
Citations number
47
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
28
Year of publication
1995
Pages
4955 - 4958
Database
ISI
SICI code
0040-4039(1995)36:28<4955:SONNDA>2.0.ZU;2-U
Abstract
A general route for the preparation of N alpha-alkylated and N-beta-al kylated derivatives of diaminopropionic acids is described. Nucleophil ic ring opening of N-tosyl aziridine-2-t-butyl carboxylate with primar y amines leads to the corresponding N-beta-alkyl derivative. Reaction of the N-beta-tosyl diaminopropionic derivative with Cs2CO3 and alkyl iodide selectively produces the N-alpha-alkylated compound.