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Synthesis 1988; 1988(2): 136-138
DOI: 10.1055/s-1988-27491
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Synthesis of Functionalized β-Amino α,β-Unsaturated Esters and Nitriles by Nucleophilic Vinylic Substitution

Begoña de Ancos* , M. Carmen Maestro, M. Rosario Martín, Francisco Fariña
  • *Departamento de Química C-1, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid, Spain
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Publication Date:
20 August 2002 (online)

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The nucleophilic vinylic substitution of halogen by primary and secondary amines on methyl (E)- and (Z)-3-bromo-4,4-dimethoxy-2-butenoates (1) and the corresponding nitriles (2) leads to methyl 3-amino-4,4-dimethoxy-2-butenoates and the corresponding nitriles, respectively, in good yields. The stereochemistry of the reactions has also been studied.