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Synthesis 2009(18): 3047-3050  
DOI: 10.1055/s-0029-1216896
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantiotopic Discrimination in Palladium-Mediated Nucleophilic Substitu­tions on Achiral Substrates: Chiral Ligand versus Chiral Nucleophile

Olivier Jacqueta, Florence Charnayb, Jean-Claude Fiaud*a, Jean Ollivier*b
a Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université de Paris-Sud 11, 91405 Orsay, France
Fax: +33(1)69154680; e-Mail: fiaud@icmo.u-psud.fr;
b Laboratoire de Synthèse Organique et Méthodologie, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université de Paris-Sud 11, 91405 Orsay, France
Fax: +33(1)69156278; e-Mail: jollivie@icmo.u-psud.fr;
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Publication History

Received 24 April 2009
Publication Date:
10 July 2009 (online)

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Abstract

The Tsuji-Trost reaction performed on an achiral allylic ester using a chiral ligand-achiral nucleophile couple or a achiral ligand-chiral nucleophile couple, afforded optically enriched β-vinylcyclohexenyl amines. Thus, the hypothesis of a differentiation between two diastereotopic allylic sites of a π-allyl palladium complex by a nucleophile, confirm previous observations.

Key words

nucleophilic substitutions - π-allyl palladium complexes - cyclopropylidenes - cyclohexenes - amines