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Stereoselective Cycloaddition of Monosubstituted Ketene to a Methyl Glyoxylate- and Threonine-Derived Imine: Synthesis of Optically Pure β-Lactamic α-Amino Ester with High Functionality |
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| Authors: | Serge Mignani Dominique Mouysset Isabelle Le Roy Lucien Stella |
| Institution: | 1. Rh?ne-Poulenc Rorer, Centre de Recherche , 13 Quai Jules Guesde, BP 14, 94403, Vitry sur Seine, Cedex, France;2. Université d'Aix-Marseille III, Laboratoire de Chimie Moléculaire Organique UMR 6517 , 13397, Marseille, Cedex 20, France;3. Université d'Aix-Marseille III, Laboratoire de Chimie Moléculaire Organique UMR 6517 , 13397, Marseille, Cedex 20, France |
| Abstract: | The reaction of chloroacetyl chloride and triethylamine with a chiral imine derived from the combination of methyl glyoxylate and protected L-threonine gave two optically active α-amino acid derivatives with a cis-substituted β-lactam skeleton in a 72:28 ratio. The major product is obtained in 59% yield by simple crystallisation. |
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