Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates

S D Bull, S G Davies, S W Epstein, A C Garner, N Mujtaba, E D Savory, Andrew David Smith, J A Tamayo, D J Watkin

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7911
Number of pages7911
JournalTetrahedron
Volume62
DOIs
Publication statusPublished - 14 Aug 2006

Keywords

  • enantiodiscrimination
  • diketopiperazine
  • 3-methyl-aspartate
  • ALPHA-AMINO-ACIDS
  • ANTIMITOTIC BICYCLIC PEPTIDES
  • MAXIMUM OPTICAL ROTATIONS
  • CHIRAL RELAY AUXILIARY
  • KINETIC RESOLUTION
  • STEREOSELECTIVE-SYNTHESIS
  • 3-ALKYLALKANOIC ACIDS
  • CONJUGATE ADDITIONS
  • OXIDATIVE ADDITION
  • CELOSIA-ARGENTEA

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