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Amino acids and peptides. XV. A new synthesis of .ALPHA.-amino acids by amination of .ALPHA.-metalated carboxylic acids.

1975; Pharmaceutical Society of Japan; Volume: 23; Issue: 1 Linguagem: Inglês

10.1248/cpb.23.167

1347-5223

T. OGURI, Takayuki Shioiri, Shun‐ichi Yamada,

Chemical Synthesis and Analysis

Amination of α-lithiated carboxylic acid salts was investigated using isovaleric acid mainly. Methoxyamine bearing a proper electronic character was the best aminating reagent, as shown in Table I. Several α-amino acids, e.g., valine, leucine, methionine, phenylalanine, and α-phenylglycine, were prepared by this new method, summarized in Table II. The synthesis of two new aminating reagents, 3, 5-dinitromesitoxyamine and 2-tetrahydropyranyloxyamine were described.