4.6 Article

Multistereogenic Phosphine Ligand-promoted Palladium-Catalyzed Allylic Alkylation of Cyanoesters

Journal

CHEMCATCHEM
Volume 7, Issue 1, Pages 75-79

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201402733

Keywords

alkylation; allyl compounds; asymmetric catalysis; multistereogenic centers; palladium

Funding

  1. National Natural Science Founder of China [21173064, 21472031]
  2. Zhejiang Provincial Natural Science Foundation of China [LR14B030001]

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A palladium-catalyzed allylic alkylation of unsubstituted 2-cyanoacetates using a 1,1'-bi-2-naphthol-derived multifunctional N,O,P ligand is reported. A number of chiral monosubstituted 2-cyanoacetates with two adjacent stereogenic carbon centers are obtained in this Pd-catalyzed asymmetric allylic alkylation reaction, in which the multistereogenic and multifunctional 1,1'-bi-2-naphthol-derived N,O,P ligand-promoted Pd-catalyzed asymmetric allylic alkylation reaction proceeds smoothly in high diastereo- and enantioselectivity (up to > 99:1 dr and up to 96% ee).

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