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Issue 17, 1998
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First asymmetric synthesis of the Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S )-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino]cyclohexane-1-carboxylic acid

Abstract

The first asymmetric synthesis of Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S )-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino]cyclohexane-1-carboxylic acid is achieved using lithium amide (R)-5 and pyrrolidinone auxiliary (R)-6; the pyrrolidinone auxiliary is used to create (2S )-benzylsuccinic acid derivative (S )-4 while lithium amide (R)-5 is used to synthesize tert-butyl (1S,2R)-2-aminocyclohexanecarboxylate 3.

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Article type: Paper
DOI: 10.1039/A804660C
Citation: J. Chem. Soc., Perkin Trans. 1, 1998,0, 2629-2634
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    First asymmetric synthesis of the Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S )-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino]cyclohexane-1-carboxylic acid

    S. G. Davies and D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 0, 2629
    DOI: 10.1039/A804660C

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