Inter- or Intramolecular Coupling of β-Haloamino Acids with Alkynes

Benoît Miossec; Renée Danion-Bougot; Daniel Danion

doi:10.1055/s-1994-25666

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Synthesis 1994; 1994(11): 1171-1174
DOI: 10.1055/s-1994-25666

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Inter- or Intramolecular Coupling of β-Haloamino Acids with Alkynes

Benoît Miossec^* , Renée Danion-Bougot, Daniel Danion

^*Groupe de Recherches de Physicochimie structurale, U.R.A. C.N.R.S. 704, Université de Rennes I, F-35042 Rennes Cédex, France

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Publication Date:
25 April 2002 (online)

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Coupling reaction of 1-alkynes with β-bromodidehydroalaninate in the presence of catalytic (PPh₃)₄Pd and CuI provides a simple approach to amino acids with a 1,3-enyne side chain. Bu₃SnH mediated cyclisation of α-(2-propynyloxy)-β-bromoamino acids allows the synthesis of methylene tetrahydrofurans with an amino acid functionality.