752233-61-7Relevant academic research and scientific papers
A new method for the preparation of functionalized unnatural α-H-α-amino acid derivatives
Hyett, David J.,Didonè, Mara,Milcent, Thierry J.A.,Broxterman, Quirinus B.,Kaptein, Bernard
, p. 7771 - 7774 (2007/10/03)
A new method for the preparation of α-H-α-amino acids is reported based on the α-alkylation of iminoacetic acid esters or amides. These imines are readily available by the reaction of glyoxylic acid esters with branched primary amines. The subsequent reaction with methanolic ammonia gave the corresponding iminoacetic acid amides. α-Alkylation of these imines with various electrophiles under basic conditions, followed by an acidic hydrolysis, gave α-amino acids, esters, or amides in up to 93% yield. α-Alkylation under chiral PTC conditions resulted in mono-alkylated amino acids with 90% ee.
The regioselective α-alkylation of the benzophenone imine of glycinamide, alaninamide, and related derivatives
O'Donnell, Martin J.,Keeton, Jeremy D.,Van Khau, Vien,Bollinger, John C.
, p. 1301 - 1312 (2007/10/03)
The benzophenone imine of glycinamide was alkylated using ion pair extraction (RX, 10% aq. NaOH, Bu4NHSO4 (1 equiv.), CH 2Cl2, rt) to give the α-monosubstituted products, which were then alkylated a second time
PROCESS FOR THE PREPARATION OF AN α-AMINO CARBONYL COMPOUND
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Page 18-19, (2008/06/13)
The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.
