New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids

MJ Crossley, YM Fung, JJ Potter

Index: Crossley, Maxwell J.; Fung, Yik M.; Kyriakopoulos, Efstathia; Potter, Jeffrey J. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 6 p. 1123 - 1130

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Abstract

Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N, O-protected dehydroalanines derivable from the ...