Enzymic kinetic resolution of. alpha.-nitro. alpha.-methyl carboxylic acids

JJ Lalonde, DE Bergbreiter…

Index: Lalonde, James J.; Bergbreiter, David E.; Wong, C.-H. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2323 - 2327

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Citation Number: 51

Abstract

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