28332-44-7Relevant academic research and scientific papers
Carbonylation of tertiary carbon radicals: synthesis of lactams
Yin, Zhiping,Zhang, Zhuan,Zhang, Youcan,Dixneuf, Pierre H.,Wu, Xiao-Feng
, p. 4655 - 4658 (2019/05/09)
Herein, we disclose an interesting iron-catalyzed approach for the carbonylation of a tertiary carbon radical. The tertiary carbon radical generated from a 1,5-hydrogen atom transfer can be captured by CO gas smoothly. Various six-membered lactams were constructed chemo-selectively in high yields.
Palladium catalyzed reductive decarboxylation of allyl α-alkenyl- β-ketoesters. A new synthesis of (E)-3-alkenones
Ragoussis, Valentine,Giannikopoulos, Alexandros
, p. 683 - 687 (2007/10/03)
The reductive decarboxylation of α-alkenyl derivatives of allyl-β-ketoesters was achieved by use of palladium(0) catalyst generated in situ from Pd(OAc)2 and PPh3, with triethylammonium formate as the hydride source, in THF. The reaction proceeds smoothly and cleanly, with linear alkenyl derivatives of allyl-β-ketoesters, to afford (E)-3-alkenones in good to excellent yields (73-92%) and high stereoselectivity (>98%).
The reaction of trialkylstannylmethyllithium with α,β-epoxy ketones and α-chloro ketones
Sato, Tadashi,Kikuchi, Toshihiro,Tsujita, Hiroshi,Kaetsu, Atsushi,Sootome, Norio,Nishida, Ken-Ichiro,Tachibana, Kazutaka,Murayama, Eigoro
, p. 3281 - 3304 (2007/10/02)
The reactions of trialkylstannylmethyllithium with α,β-epoxy ketones afforded mainly cyclopropanols, while α-chloro ketones afforded allyl alcohols and/or cyclopropanols, in varying amounts depending upon the molar ratio of the reagent to the substrate.
SYNTHESIS WITH MANGANIC SALTS; PART III: SYNTHESIS OF 1,4-DIKETONES THROUGH MANGANIC ACETATE-MEDIATED ADDITION OF KETONE TO ISOPENTENYL SULFONES. ACETOXYLATION OF Β,Γ-UNSATURATED KETONES BY MANGANOUS AND CUPRIC ACETATES
Breuilles, Pascal,Uguen, Daniel
, p. 705 - 720 (2007/10/02)
Conditions have been found to selectively add ketones to isopentenyl sulfones.The major product, a ketone bearing a methylene group at the γ position, gave upon ozonolysis the corresponding 1,4-diketone.The usefulness of the overall process was illustrated by the efficient syntheses of jasmone and of one half of pyrenophorine.The γ-acetoxy conjugated enones that invariably formed during these additions resulted from the oxidation of an isomeric β,γ-unsaturated ketone by manganous and cupric acetates.Such an acetoxylation has been used to prepare 6β-acetoxy-cholestenone from cholesterol and also to prepare chrysanthemic acid.
THE REACTION OF TRIALKYLSTANNYLMETHYLLITHIUM WITH α,β-EPOXY KETONES. A PREPARATIVE METHOD OF β,γ-UNSATURATED KETONES BY HOMOLOGATION OF α,β-UNSATURATED KETONES
Sato, Tadashi,Kikuchi, Toshihiro,Sootome, Norio,Murayama, Eigoro
, p. 2205 - 2208 (2007/10/02)
α,β-Epoxy ketones 2, upon treatment with two equivalents of trialkylstannylmethyllithium 1, afforded cyclopropanols 3 as a single product in acyclic system, and a mixture of cyclopropanols 3 and methylene 1,2-diols 4 in cyclic system.Under acidic conditions, the cyclopropanols gave β,γ-unsaturated ketones 5 in good yields.
REACTIVITE DU DERIVE LITHIE ISSU DU DIOXOLANNE DU LEVULATE DE TRIMETHYLSILYLE VIS-A-VIS DES DERIVES CARBONYLES: UNE METHODE DIRECTE D'OLEFINATION DES ALDEHYDES AROMATIQUES ET DES CETONES
Moreau, Jean-Louis,Couffignal, Rene
, p. 1 - 12 (2007/10/02)
At -60 deg C and in ether, the organolithium reagent produced by trimethylsilyl 4,4-ethylenedioxypentanoate reacts with aldehydes and ketones, and gives the expected β-hydroxyacids.The β-ethylenic ketones are isolated when the condensation is carried out
Synthesis of Chloromethylvinylcyclopropanecarboxylic Acid Derivatives
Muramatsu, Shigeki,Nakada, Yasuo,Ide, Junya
, p. 751 - 760 (2007/10/02)
The compound 3-(2-chloro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate, which is a hybrid structure of naturally occuring chrysanthemic acid and dichlorovinylcyclopropanecarboxylate, was synthesized from several intermediates: (i) 5-methyl-4-hexen-2-one ethylene ketal (8), (ii) 2-methyl-5,5-dichloro-2-hexene (24), (iii) 5-methyl-2-chloro-2,4-hexadiene (27), (iv) ethyl 4,6-dichloro-3,3-dimethyl-5-heptenoate (35).
Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex
Kosugi, Masanori,Hagiwara, Isao,Sumiya, Takao,Migita, Toshihiko
, p. 241 - 246 (2007/10/02)
The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with aryl and 1-alkenyl bromides in the presence of dichlorobis(tri-o-tolylphosphine)palladium was found to give α-aryl and α-(1-alkenyl) ketones, respectively, in good yields with essentially complete retention of the enol acetate regiochemistry.
ZIRCONIUM ASSISTED REGIOSELECTIVE ACYLATION OF DIENES WITH SATURATED OR UNSATURATED ESTERS TO LEAD TO β,γ-UNSATURATED CARBONYL COMPOUNDS
Akita, Munetaka,Yasuda, Hajime,Nakamura, Akira
, p. 217 - 218 (2007/10/02)
Regioselective formylation or acylation of isoprene at the C1 atom was realized by reaction of Cp2Zr(isoprene) with saturated esters followed by protonolysis with acetic acid.The corresponding reaction with various alkyl acrylates resulted in the formatio
1-ALKENYLATION ON α-POSITION OF KETONE: PALLADIUM-CATALYZED REACTION OF TIN ENOLATES AND 1-BROMO-1-ALKENES
Kosugi, Masanori,Hagiwara, Isao,Migita, Toshihiko
, p. 839 - 840 (2007/10/02)
The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with 1-bromo-1-alkenes in the presence of a catalytic amount of PdCl2(o-tolyl3P)2 was found to give the derivatives of allyl ketone in good yields.
