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Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology.

Abstract:

Diketopiperazinespirocyclopropane 12 is prepared in > 98% d.e. via the conjugate addition of a phosphorus ylide to (6S)-N,N'-bis(p-methoxybenzyl)-3-methylenepiperazine-2,5-dione 2. Deprotection and hydrolysis of adduct 12 and subsequent peptide coupling demonstrate the applicability of this methodology to the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids for incorporation into novel peptides. A model for the high level of diastereofacial selectivity observed in the cyclopr...

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Publication status:
Published

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Publisher copy:
10.1039/b303348a

Authors


Buñuel, E More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Garner, AC More by this author
Savory, ED More by this author
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Journal:
Organic and biomolecular chemistry
Volume:
1
Issue:
14
Pages:
2531-2542
Publication date:
2003-07-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:d308c1f1-4a15-4322-8571-bf92f459fa00
Source identifiers:
32450
Local pid:
pubs:32450
Language:
English

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