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

被引：14

作者：

Davies, SG ^{[1
]}

Dixon, DJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 17期

关键词：

D O I：

10.1039/a804660c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2629 / 2634

页数：6

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