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Issue 5, 1997
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Reaction of organolead triacetates with4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis ofα-aryl- and α-vinyl-N-acetylglycines andtheir ethyl esters and their enzymic resolution

Jacqueline Morgan,  John T. Pinhey  and  Christopher J. Sherry 

Abstract

4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 7, which may be readily obtained from diethyl acetamidomalonate, undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which may be hydrolysed to give either the α-aryl- or α-vinyl-N-acetylglycine or the corresponding ethyl ester. The kinetic resolution of a number of these derivatives by enzymic hydrolysis of either the amide or ester function has been demonstrated.

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Article type: Paper
DOI: 10.1039/A606309H
Citation: J. Chem. Soc., Perkin Trans. 1, 1997,0, 613-620
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    Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution

    J. Morgan, J. T. Pinhey and C. J. Sherry, J. Chem. Soc., Perkin Trans. 1, 1997, 0, 613
    DOI: 10.1039/A606309H

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