Journal of Organic Chemistry p. 2323 - 2327 (1988)
Update date:2022-07-31
Topics:
Lalonde, James J.
Bergbreiter, David E.
Wong, C.-H.
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.
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