148150-70-3Relevant academic research and scientific papers
Synthesis of a chiral serine aldehyde equivalent and its conversion to chiral α-Amino acid derivatives
Blaskovich, Mark A.,Lajoie, Gilles A.
, p. 5021 - 5030 (2007/10/02)
We report a new methodology for the synthesis of chiral nonproteinaceous α-amino acids, which involves protection of the carboxyl group of serine as a cyclic ortho ester. This reduces the acidity of the α-proton, allowing for oxidation of the side chain of serine to an aldehyde without racemization. A variety of carbonyl addition reactions, such as Grignard, Reformatsky, and Wittig additions, can then be carried out, leading to a wide range of amino acids. Very good stereocontrol is achieved, allowing for the selective synthesis of all four diastereomers of β-hydroxy-α-amino acids. The method readily allows for stereospecific incorporation of both C and H isotopes in amino acid side chains.
