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Palladium-catalyzed Saegusa-Ito oxidation: synthesis of α,β-unsaturated carbonyl compounds from trimethylsilyl enol ethers.
J Org Chem. 2013 Jan 18; 78(2):776-9.JO

Abstract

Palladium-catalyzed Saegusa-Ito oxidation of trimethylsilyl enol ethers is possible using Oxone as a stoichiometric oxidant and sodium hydrogen phosphate as a buffer. Cyclic and acyclic enones as well as α,β-unsaturated aldehydes are obtained in good to excellent yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Lu Y
Department of Chemistry and Centre in Green Chemistry and Catalysis (CGCC), Université de Montréal, Pavillon Roger Gaudry, 2900 Boul. Édouard-Montpetit, Montréal, Québec, Canada, H3T 1J4.
Nguyen PL
No affiliation info available
Lévaray N
No affiliation info available
Lebel H
No affiliation info available

MeSH

AlcoholsAldehydesCatalysisEthersKetonesMolecular StructureOxidation-ReductionPalladiumStereoisomerismTrimethylsilyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23256839

Citation

Lu, Yingdong, et al. "Palladium-catalyzed Saegusa-Ito Oxidation: Synthesis of Α,β-unsaturated Carbonyl Compounds From Trimethylsilyl Enol Ethers." The Journal of Organic Chemistry, vol. 78, no. 2, 2013, pp. 776-9.
Lu Y, Nguyen PL, Lévaray N, et al. Palladium-catalyzed Saegusa-Ito oxidation: synthesis of α,β-unsaturated carbonyl compounds from trimethylsilyl enol ethers. J Org Chem. 2013;78(2):776-9.
Lu, Y., Nguyen, P. L., Lévaray, N., & Lebel, H. (2013). Palladium-catalyzed Saegusa-Ito oxidation: synthesis of α,β-unsaturated carbonyl compounds from trimethylsilyl enol ethers. The Journal of Organic Chemistry, 78(2), 776-9. https://doi.org/10.1021/jo302465v
Lu Y, et al. Palladium-catalyzed Saegusa-Ito Oxidation: Synthesis of Α,β-unsaturated Carbonyl Compounds From Trimethylsilyl Enol Ethers. J Org Chem. 2013 Jan 18;78(2):776-9. PubMed PMID: 23256839.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed Saegusa-Ito oxidation: synthesis of α,β-unsaturated carbonyl compounds from trimethylsilyl enol ethers. AU - Lu,Yingdong, AU - Nguyen,Pierre Long, AU - Lévaray,Nicolas, AU - Lebel,Hélène, Y1 - 2013/01/10/ PY - 2012/12/22/entrez PY - 2012/12/22/pubmed PY - 2013/9/11/medline SP - 776 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 78 IS - 2 N2 - Palladium-catalyzed Saegusa-Ito oxidation of trimethylsilyl enol ethers is possible using Oxone as a stoichiometric oxidant and sodium hydrogen phosphate as a buffer. Cyclic and acyclic enones as well as α,β-unsaturated aldehydes are obtained in good to excellent yields. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/23256839/Palladium_catalyzed_Saegusa_Ito_oxidation:_synthesis_of_αβ_unsaturated_carbonyl_compounds_from_trimethylsilyl_enol_ethers_ L2 - https://doi.org/10.1021/jo302465v DB - PRIME DP - Unbound Medicine ER -