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Buñuel E, Bull SD, Davies SG, et al. Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology. Org Biomol Chem. 2003;1(14):2531-42doi: 10.1039/b303348a.
Buñuel, E., Bull, S. D., Davies, S. G., Garner, A. C., Savory, E. D., Smith, A. D., Vickers, R. J., & Watkin, D. J. (2003). Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology. Organic & biomolecular chemistry, 1(14), 2531-42. https://doi.org/10.1039/b303348a
Buñuel, Elena, et al. "Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology." Organic & biomolecular chemistry vol. 1,14 (2003): 2531-42. doi: https://doi.org/10.1039/b303348a
Buñuel E, Bull SD, Davies SG, Garner AC, Savory ED, Smith AD, Vickers RJ, Watkin DJ. Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology. Org Biomol Chem. 2003 Jul 21;1(14):2531-42. doi: 10.1039/b303348a. PMID: 12956073.
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Org Biomol Chem. 2003 Jul 21;1(14):2531-42. doi: 10.1039/b303348a.

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

Organic & biomolecular chemistry

Elena Buñuel, Steven D Bull, Stephen G Davies, A Christopher Garner, Edward D Savory, Andrew D Smith, Richard J Vickers, David J Watkin

Affiliations

  1. Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK OX1 3QY.

PMID: 12956073 DOI: 10.1039/b303348a

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 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.

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