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Asymmetric synthesis of the stereoisomers of 2-amino-5-carboxymethyl-cyclopentane-1-carboxylate.

Abstract:

The stereoisomers of 2-amino-5-carboxymethyl-cyclopentane-1-carboxylate may be prepared stereoselectively from diester derivatives of (E,E)-octa-2,6-diendioc acid, with the key step utilising the conjugate addition of homochiral lithium N-benzyl-N- alpha-methylbenzylamide. The trans-C(1)-C(2)-stereoisomers are readily prepared via a diastereoselective tandem conjugate addition cyclisation protocol with lithium (R)-N-benzyl-N- alpha-methylbenzylamide, with subsequent hydrogenolysis and ester h...

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Publication status:
Published

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Publisher copy:
10.1039/b313386a

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Journal:
Organic and biomolecular chemistry More from this journal
Volume:
2
Issue:
3
Pages:
364-372
Publication date:
2004-02-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Language:
English
Pubs id:
pubs:110581
UUID:
uuid:28c6a3e8-764b-4248-89cf-094ab5ac0556
Local pid:
pubs:110581
Source identifiers:
110581
Deposit date:
2012-12-19

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