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Issue 14, 2003
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Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids viadiketopiperazine methodology

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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)-[2,2-2H2]-1-aminocyclopropane-1-carboxylic acid 29 is also reported via a deuterated sulfur ylide addition to acceptor 2.

Graphical abstract: Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids via diketopiperazine methodology

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Supplementary files

Article information


Submitted
04 Apr 2003
Accepted
02 Jun 2003
First published
19 Jun 2003

Org. Biomol. Chem., 2003,1, 2531-2542
Article type
Paper

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

E. Buñuel, S. D. Bull, S. G. Davies, A. C. Garner, E. D. Savory, A. D. Smith, R. J. Vickers and D. J. Watkin, Org. Biomol. Chem., 2003, 1, 2531
DOI: 10.1039/B303348A

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