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Synlett 1995; 1995(10): 1067-1068
DOI: 10.1055/s-1995-5187
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Stereoselective Synthesis of Monocyclic β-Lactam Related to a Carmonam Precursor via Ketene-Imine Reaction

Tamotsu Fujisawa* , Akinori Shibuya, Daisuke Sato, Makoto Shimizu
  • *Department of Chemistry for Materials, Mie University, Tsu, Mie 514, Japan
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Publication Date:
31 December 2000 (online)

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Reaction of chiral imine derived from (L)-malic acid with acid chlorides from glycine derivatives in the presence of triethylamine afforded optically active cis-substituted β-lactam, which in turn was transformed into a carmonam precursor with excellent stereoselectivity.

(L)-malic acid - ketene-imine reaction - carmonam precursor - high diastereoselectivity

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