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Synlett 2001; 2001(6): 0781-0784
DOI: 10.1055/s-2001-14596
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The Asymmetric Synthesis of (2R,3R)- and (2R,3S)-3-Methyl-aspartates via an Enantiodiscrimination Strategy

Steven D. Bull* , Stephen G. Davies, A. Christopher Garner, Nadeam Mujtaba
  • *The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK; E-mail: steve.davies@chemistry.ox.ac.uk
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Publication History

Publication Date:
31 December 2001 (online)

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The enolate of (S)-N,N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibits high levels of enantiodiscrimination towards racemic 2-bromo-propionate esters of afford adducts containing two new stereogenic centers which may be deprotected to afford (2R,3R)-3-methyl-aspartates or epimerised and then deprotected to afford (2R,3S)-3-methyl-aspartates as single diastereoisomers in high e.e.

enantiodiscrimination - diketopiperazine auxiliary - 3-alkylaspartates - asymmetric synthesis

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