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Synthesis 1997; 1997(7): 747-749
DOI: 10.1055/s-1997-3184
short paper
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A Convenient Synthesis of L-α-Vinylglycine from D-Mannitol

Ramón Badorrey, Carlos Cativiela1 , María D. Díaz-de-Villegas2 , José A. Gálvez
  • 1Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Universidad de Zaragoza-C.S.I.C., 50009 Zaragoza, Spain, Fax +34(76)761159; E-mail:carlos.cativiela@msf.unizar.es
  • 2Instituto de Ciencia de Materiales de Aragón, Departamento de Química Orgánica, Universidad de Zaragoza-C.S.I.C., 50009 Zaragoza, Spain, Fax +34(76)761159; E-mail: lola.diazdv@msf.unizar.es
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Publication Date:
31 December 2000 (online)

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A novel procedure is described for the synthesis of L-α-vinylglycine based on the diastereoselective addition of vinylmagnesium bromide to the N-benzyl imine derived from 2,3-0-isopropylidene-D-glyceraldehyde. The route developed is both convenient (only one diastereoisomer is obtained in the addition reaction) and efficient (45% overall yield over 7 steps).

diastereoselective organometallic addition - D-mannitol - L-α-vinylglycine - asymmetric synthesis - α-amino acids

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