(R)-2-Phenylglycine as a chiral auxiliary in the asymmetric synthesis of 2-azetidinones

H.L. Van Maanen, J.T.B.H. Jastrzebski, J. Verweij, A.P.G. Kieboom, A.L. Spek, G. Van Koten

Research output: Contribution to journalArticleAcademicpeer-review


The chlorozinc enolate of ethyl-[(2,2,5,5-tetramethyl-1-aza-2,5-disila)cyclopentyl]acetate was reacted with the ZnCl2complex of N-benzylidene-2-phenylglycine methyl ester in THF at -70°C. After removal of the protecting silyl moiety (3S, 4S, αR)-1-(methoxycarbonyl)(phenyl)methyl-3-amino-4-phenyl-2-azetidinone was obtained in 73% yield with >97% d.e.. By treatment with aqueous ammonia complete epimerization at the α-position was accomplished. The (3S, 4S, αS) enantiomer was crystallized from THF and the absolute configuration was determined by X-Ray crystallography.
Original languageEnglish
Pages (from-to)1441-1444
Number of pages4
Issue number7
Publication statusPublished - 12 Mar 1993


  • azetidinone derivative
  • article
  • drug synthesis
  • reaction analysis
  • X ray crystallography


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