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Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates.
J Org Chem. 2008 Sep 05; 73(17):6828-30.JO

Abstract

Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group was necessary in the methylenation process.

Authors+Show Affiliations

Département de Chimie, Université de Montréal, Pavillon Roger Gaudry, 2900 Boul. Edouard-Montpetit, Montréal, Québec, Canada H3T 1J4. helene.lebel@umontreal.caNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18661948

Citation

Lebel, Hélène, et al. "Transition-metal-catalyzed Chemoselective Methylenation of Dicarbonyl Substrates." The Journal of Organic Chemistry, vol. 73, no. 17, 2008, pp. 6828-30.
Lebel H, Davi M, Stokłosa GT. Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates. J Org Chem. 2008;73(17):6828-30.
Lebel, H., Davi, M., & Stokłosa, G. T. (2008). Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates. The Journal of Organic Chemistry, 73(17), 6828-30. https://doi.org/10.1021/jo800777w
Lebel H, Davi M, Stokłosa GT. Transition-metal-catalyzed Chemoselective Methylenation of Dicarbonyl Substrates. J Org Chem. 2008 Sep 5;73(17):6828-30. PubMed PMID: 18661948.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transition-metal-catalyzed chemoselective methylenation of dicarbonyl substrates. AU - Lebel,Hélène, AU - Davi,Michaël, AU - Stokłosa,Grzegorz T, Y1 - 2008/07/29/ PY - 2008/7/30/pubmed PY - 2008/12/17/medline PY - 2008/7/30/entrez SP - 6828 EP - 30 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 17 N2 - Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group was necessary in the methylenation process. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18661948/Transition_metal_catalyzed_chemoselective_methylenation_of_dicarbonyl_substrates_ L2 - https://doi.org/10.1021/jo800777w DB - PRIME DP - Unbound Medicine ER -