Isolation and Characterization of a Chiral η1-Allyl Palladium DIPPAM Complex: Application to the Enantioselective Pd-Catalyzed Allylic Alkylation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organometallics Année : 2010

Isolation and Characterization of a Chiral η1-Allyl Palladium DIPPAM Complex: Application to the Enantioselective Pd-Catalyzed Allylic Alkylation

Résumé

In the presence of [Cl(C3H5)Pd]2, diphenylphosphinoazomethinylate salt (DIPPAM) 1a forms an original chiral η1-allyl palladium complex, 2. Precatalyst 2/MgBr2 is an efficient catalyst for asymmetric allylic alkylation, giving good yields and ee's in the reactions of rac-4-acetoxy-2-pentene or rac-3-acetoxy-1,3-diphenyl-1-propene and dimethyl malonate (respectively 77% and 96% yield; 66% and 96% ee). Preliminary mechanistic studies have highlighted the key role of the η1-coordination mode of the allyl fragment.

Domaines

Chimie organique
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Dates et versions

hal-00759118 , version 1 (30-11-2012)

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Citer

Joanna Wencel, Isabelle Laurent, Loïc Toupet, Christophe Crévisy, Marc Mauduit. Isolation and Characterization of a Chiral η1-Allyl Palladium DIPPAM Complex: Application to the Enantioselective Pd-Catalyzed Allylic Alkylation. Organometallics, 2010, 29 (7), pp.1530-1533. ⟨10.1021/om100061q⟩. ⟨hal-00759118⟩
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