… asymmetric synthesis of the Kelatorphan-like enkephalinase inhibitor (1 S, 2 R, 2′ S)-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino] cyclohexane-1 …

SG Davies, DJ Dixon

Index: Davies, Stephen G.; Dixon, Darren J. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2629 - 2634

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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- ...