478074-23-6Relevant academic research and scientific papers
Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters
Karad, Somnath Narayan,Panchal, Heena,Clarke, Christopher,Lewis, William,Lam, Hon Wai
supporting information, p. 9122 - 9125 (2018/07/24)
The enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline/nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6-dihydropyridin-3(2H)-ones.
Direct Esterification of Carboxylic Acids with Perfluorinated Alcohols Mediated by XtalFluor-E
Vandamme, Mathilde,Bouchard, Léa,Gilbert, Audrey,Keita, Massaba,Paquin, Jean-Fran?ois
supporting information, p. 6468 - 6471 (2016/12/23)
The direct esterification of carboxylic acids with perfluorinated alcohols mediated by XtalFluor-E is reported. The corresponding polyfluorinated esters are obtained in moderate to excellent yields with a broad range of carboxylic acids, including aromati
Azodicarbonyl dimorpholide (ADDM): An effective, versatile, and water-soluble Mitsunobu reagent
Lanning, Maryanna E.,Fletcher, Steven
, p. 4624 - 4628 (2013/08/23)
One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented.
Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates
Takacs, James M.,Xu, Zhenrong,Jiang, Xun-Tian,Leonov, Alexei P.,Theriot, Gregory C.
, p. 3843 - 3845 (2007/10/03)
(Matrix Presented) Simple dialkyl malonate esters, for example diethyl malonate, exhibit relatively limited scope as carbon nucleophiles in the Mitsunobu dehydrative alkylation reaction. In contrast, bis(2,2,2-trifluoroethyl) malonate readily undergoes dehydrative alkylation with primary alcohols, and using only a slight excess of malonate gives monoalkylated product in good yield. Some secondary alcohols can also be employed, and bis(2,2,2-trifluoroethyl) malonates can be used in a second dehydrative alkylation to give dialkylated products in good to excellent yield.
