1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Philip C. Bulman Page; Harry Heaney; Serge Reignier; Gerasimos A. Rassias

doi:10.1055/s-2003-36221

LETTER

1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Philip C. Bulman Page*, Harry Heaney, Serge Reignier, Gerasimos A. Rassias
Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, England
Fax: +44(1509)223926; e-Mail: p.c.b.page@lboro.ac.uk;

Abstract

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Abstract

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89%. The stereoelectronic effects operating in the reactions are discussed.

Key words

ephedrine - heterobidentate ligands - allylic substitution

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