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Synlett 2001; 2001(12): 1813-1826
DOI: 10.1055/s-2001-18733
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β-Lactams as Versatile Intermediates in α- and β-Amino Acid Synthesis

Claudio Palomo* , Jesús M. Aizpurua, Iñaki Ganboa, Mikel Oiarbide
  • *Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain; Fax: + 34(943)212236; E-mail: qoppanic@sc.ehu.es
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Publication Date:
04 December 2001 (online)

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The use of β-lactams as synthetic intermediates has recently found considerable interest, driven by the accessibility of enantiomerically pure β-lactam building-blocks and by the discovery of selective methods for the β-lactam ring opening. N 1-C 2 and C 2-C 3 bond cleavage of β-lactams can now be effected cleanly by different nucleophiles, in an intra- or intermolecular fashion, under isomerization-free conditions. By this way, an array of diverse, densely functionalized, cyclic as well as open chain, α- and β-amino acid derivatives, including peptides, have been synthesized. Examples from our laboratory and from others are provided.

β-lactams - β-amino acids - α-amino acids - peptides