Issue 13, 2007
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates†

Stephen G. Davies,*a   A. Christopher Garner,a   Jaqueline V. A. Ouzman,a   Paul M. Roberts,a   Andrew D. Smith,a   Emma J. Snow,a   James E. Thomson,a   Juan A. Tamayoa  and  Richard J. Vickersa  

* Corresponding authors

a Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk

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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Article information

DOI
https://doi.org/10.1039/B704475E
Article type
Paper
Submitted
23 Mar 2007
Accepted
17 May 2007
First published
29 May 2007

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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