| Autor: |
Buñuel E; Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY., Bull SD, Davies SG, Garner AC, Savory ED, Smith AD, Vickers RJ, Watkin DJ |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2003 Jul 21; Vol. 1 (14), pp. 2531-42. |
| DOI: |
10.1039/b303348a |
| Abstrakt: |
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 cyclopropanation reaction is presented. A highly selective asymmetric approach (> 98% d.e.) to (S)-[2,2-(2)H2]-1-aminocyclopropane-1-carboxylic acid 29 is also reported via a deuterated sulfur ylide addition to acceptor 2. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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