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Issue 13, 2007
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Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates

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Abstract

Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

Graphical abstract: Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates

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Publication details

The article was received on 23 Mar 2007, accepted on 17 May 2007 and first published on 29 May 2007


Article type: Paper
DOI: 10.1039/B704475E
Citation: Org. Biomol. Chem., 2007,5, 2138-2147
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    Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates

    S. G. Davies, A. Christopher Garner, J. V. A. Ouzman, P. M. Roberts, A. D. Smith, E. J. Snow, J. E. Thomson, J. A. Tamayo and R. J. Vickers, Org. Biomol. Chem., 2007, 5, 2138
    DOI: 10.1039/B704475E

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