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Facile Stereoselective Synthesis of Gamma-Substituted Gamma-Amino Acids From the Corresponding Alpha-Amino Acids

  1. Author:
    Smrcina, M.
    Majer, P.
    Majerova, E.
    Guerassina, T. A.
    Eissenstat, M. A.

  2. Author Address

    Smrcina M NCI FREDERICK CANC RES & DEV CTR SAIC STRUCT BIOCHEM PROGRAM FREDERICK, MD 21702 USA
    1. Year: 1997
  2. Journal: Tetrahedron
    1. 53
    2. 38
    3. Pages: 12867-12874
  4. Type of Article: Article
  1. Abstract:

    A facile stereoselective method for the synthesis of gamma-substituted, gamma-amino acids from alpha-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of alpha-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields, the corresponding gamma-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. (C) 1997 Elsevier Science Ltd. [References: 21]

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