Enzymatic Kinetic Resolution of α-Nitro α-Methyl Carboxylic Acids

Article abstract of DOI:10.1021/jo00245a036

Synthetic routes to various quaternary α-nitro α-methyl carboxylic acid esters from simpler nitroalkanes and nitroalkane derivatives are described.These quaternary α-amino acid precursors can be kinetically resolved by using α-chymotrypsin.It was found that partial hydrolysis of these α-nitro α-methyl esters and recovery of the unhydrolyzed ester proceeds preferentially by hydrolysis of the D enantiomer.Reduction of the α-nitro group thus then affords highly enantiomerically enriched L-α-methyl α-amino acids.