Jump to main content
Jump to site search

Issue 14, 2003
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Apr 2003, accepted on 02 Jun 2003 and first published on 19 Jun 2003


Article type: Paper
DOI: 10.1039/B303348A
Citation: Org. Biomol. Chem., 2003,1, 2531-2542
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements