250264-92-7Relevant academic research and scientific papers
Enantiomerically pure tetrahydropyrimidinones in asymmetric synthesis: Preparation of a protected α-methylasparagine derivative and corresponding dipeptides
Hopkins, Stephanie A.,Ritsema, Todd A.,Konopelski, Joseph P.
, p. 7885 - 7889 (2007/10/03)
Methyl ester 5a, available in enantiomerically pure form from the amino acid asparagine via a one-pot cyclization/protection sequence, followed by esterification, can be effectively deprotonated with LDA/DMPU/LiCl. Treatment with MeI affords the corresponding alkylated adduct in enantiomerically pure form, from which α-methylaspartic acid is obtained. Variation of the amine protection group allows for the isolation of a protected carboxylic acid/free amine derivative of α-methylasparagine. The utility of H-MeAsn-OMe is demonstrated in the formation of dipeptides.
