The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)

Yuri N. Belokon, R. Gareth Davies, José A. Fuentes, Michael North, Teresa Parsons

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Systematic variation of the substrate structure has shown that the most effective substrates for Cu(ch-salen)-catalyzed asymmetric enolate alkylation reactions carried out under phase-transfer conditions are the para-chlorophenyl imines of amino esters. The other reaction parameters (solvent and stirring speed) have also been optimized. The introduction of substituents onto the aryl rings of the salen ligand was found not to have a beneficial effect on the enantioselectivity of the reaction
Original languageEnglish
Pages (from-to)8093-8096
JournalTetrahedron Letters
Volume42
Issue number45
DOIs
Publication statusPublished - 5 Nov 2001

Keywords

  • alpha-amino-acids
  • practical asymmetric-synthesis
  • phase transfer catalysis
  • derivatives

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