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Synlett 2001; 2001(11): 1727-1730
DOI: 10.1055/s-2001-18090
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Synthesis of β-Lactams via Ring Opening of a Serine Derived Aziridine

John J. Turner* , Friso D. Sikkema, Dmitri V. Filippov, Gijs A. van der Marel, Jacques H.  van Boom
  • *Leiden Institute of Chemistry, Gorlaeus Laboratories, P. O. Box 9502, 2300 RA Leiden, The Netherlands; Fax + 31(71)5 27 43 07; E-mail: j.boom@chem.leidenuniv.nl
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Publication Date:
29 October 2001 (online)

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Serine derived aziridine 15 was successfully ring-opened with amino acid esters to give diaminopropionic acid derivatives in excellent yield and regioselectivity. These compounds were cyclised to form the corresponding β-lactams in good overall yield. One example was fully deprotected to give target compound 1 (n = 1, R = Me) in excellent yield.

Freidinger lactams - Mitsunobu reaction - nitrobenzenesulfonamides - aziridine - stereoselective synthesis

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