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Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: catalytic enantioselective Michael reaction with enones.
J Am Chem Soc. 2002 Sep 25; 124(38):11240-1.JA

Abstract

Generation of chiral palladium enolates from 1,3-dicarbonyl compounds with the palladium aqua complex and its application to the highly efficient catalytic enantioselective Michael reaction with enones are described. The palladium aqua complexes are likely to supply Brønsted base and Brønsted acid successively during the reaction. The former activates the carbonyl compounds to give chiral palladium enolates, and the latter cooperatively activates enones. Using a catalytic amount (2-10 mol %) of the palladium complexes, the various 1,3-dicarbonyl compounds including diketones and beta-ketoesters were converted to the desired Michael adducts in good yields (69-92%) with excellent enantiomeric excesses (89-99% ee).

Authors+Show Affiliations

Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12236717

Citation

Hamashima, Yoshitaka, et al. "Direct Generation of Nucleophilic Chiral Palladium Enolate From 1,3-dicarbonyl Compounds: Catalytic Enantioselective Michael Reaction With Enones." Journal of the American Chemical Society, vol. 124, no. 38, 2002, pp. 11240-1.
Hamashima Y, Hotta D, Sodeoka M. Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: catalytic enantioselective Michael reaction with enones. J Am Chem Soc. 2002;124(38):11240-1.
Hamashima, Y., Hotta, D., & Sodeoka, M. (2002). Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: catalytic enantioselective Michael reaction with enones. Journal of the American Chemical Society, 124(38), 11240-1.
Hamashima Y, Hotta D, Sodeoka M. Direct Generation of Nucleophilic Chiral Palladium Enolate From 1,3-dicarbonyl Compounds: Catalytic Enantioselective Michael Reaction With Enones. J Am Chem Soc. 2002 Sep 25;124(38):11240-1. PubMed PMID: 12236717.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: catalytic enantioselective Michael reaction with enones. AU - Hamashima,Yoshitaka, AU - Hotta,Daido, AU - Sodeoka,Mikiko, PY - 2002/9/19/pubmed PY - 2002/9/19/medline PY - 2002/9/19/entrez SP - 11240 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 124 IS - 38 N2 - Generation of chiral palladium enolates from 1,3-dicarbonyl compounds with the palladium aqua complex and its application to the highly efficient catalytic enantioselective Michael reaction with enones are described. The palladium aqua complexes are likely to supply Brønsted base and Brønsted acid successively during the reaction. The former activates the carbonyl compounds to give chiral palladium enolates, and the latter cooperatively activates enones. Using a catalytic amount (2-10 mol %) of the palladium complexes, the various 1,3-dicarbonyl compounds including diketones and beta-ketoesters were converted to the desired Michael adducts in good yields (69-92%) with excellent enantiomeric excesses (89-99% ee). SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12236717/Direct_generation_of_nucleophilic_chiral_palladium_enolate_from_13_dicarbonyl_compounds:_catalytic_enantioselective_Michael_reaction_with_enones_ L2 - https://doi.org/10.1021/ja027075i DB - PRIME DP - Unbound Medicine ER -
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