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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.

Original publication

DOI

10.1039/a804660c

Type

Journal article

Journal

Journal of the Chemical Society - Perkin Transactions 1

Publication Date

07/09/1998

Pages

2629 - 2634