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Synlett 1995; 1995(3): 226-228
DOI: 10.1055/s-1995-4925
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Enantiopure α-Allyl-α-Amino Acids by Pd-Catalyzed Allylation of a Camphorsultam Modified Glycine Equivalent

Katharina Voigt, Andreas Stolle, Jacques Salaün1 , Armin de Meijere2
  • 1Laboratoire des Carbocycles, Institut de Chimie Moléculaire d’Orsay, Université de Paris-Sud, F-91405 Orsay, France
  • 2Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Palladium-catalyzed allylation of the chirally modified glycine equivalent N-(diphenylmethyleneaminoacetyl)camphorsultam 2 with a number of differently substituted allyl esters gave the corresponding protected α-allyl-α-amino acids 7/8 in 19-79% yield with 67 - >90% diasteromeric excess. Deprotection by consecutive treatment with 0.5 N HCl and 0.25 N LiOH leads to enantiopure α-amino acids, as exemplified by 2-amino-4-cyclopropylidenebutyric acid 4.

α-Allyl-α-amino acids - O’Donnell glycine equivalent - chirally modified - Palladium - π-Allyl intermediates