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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.
Publication status:
Published

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Publisher copy:
10.1039/a804660c

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:
17
Pages:
2629-2634
Publication date:
1998-09-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
Language:
English
Pubs id:
pubs:36612
UUID:
uuid:09eed45a-4bb5-4f97-9529-0eddb61cbbac
Local pid:
pubs:36612
Source identifiers:
36612
Deposit date:
2012-12-19

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