54963-40-5Relevant academic research and scientific papers
Stereoselective Synthesis of Stannyl Enones via Palladium-Catalyzed and Free Radical Hydrostannation of Alkynyl Ketones with Trineophyltin Hydride
Dodero, Veronica I.,Koll, Liliana C.,Faraoni, M. Belen,Mitchell, Terence N.,Podesta, Julio C.
, p. 10087 - 10091 (2003)
A study on the addition of trineophyltin hydride (1) to alkynones under free radical (AIBN and Et3B) and palladium-catalyzed [(PPh3) 2PdCl2] conditions is reported. The results obtained indicate that the addition of 1 to eight ynones catalyzed by bis(triphenylphosphine)palladium(II) chloride led in all cases to addition products in very high yields (80-96%). These additions take place with excellent regio- and stereochemistry, leading to the α adducts as major products in seven out of the eight cases studied. Also the E adducts, resulting from a syn attack, were the only (seven cases) or the predominant (one case) products. The radical hydrostannations initiated by AIBN of ynones 2-5 with 1 led to addition products in good yields (60-88%); with the more hindered ketones 6 and 7-9 the yields obtained were lower. The radical additions initiated by triethylboron to ynones 2-6 follow a similar pattern but with lower yields; no addition products in the hydrostannation of ynones 7-9 were detected. The new acyl-substituted vinylstannanes, owing to their greater stability compared with that of their tributyl- and trimethylstannyl analogues, can be purified by column chromatography using neutral alumina (in all cases) or silica gel 60 (in most cases) as adsorbents. Full 1H, 13C, and 119Sn NMR data are given.
Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones
Komatsuki, Keiichi,Sadamitsu, Yuta,Sekine, Kohei,Saito, Kodai,Yamada, Tohru
, p. 11594 - 11598 (2017/09/11)
Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
Acid-catalyzed synthesis of α,β-disubstituted conjugated enones by a Meyer-Schuster-type rearrangement in allenols
Alcaide, Benito,Almendros, Pedro,Cembellín, Sara,Martínez Del Campo, Teresa
, p. 1070 - 1078 (2015/03/30)
A novel, direct and simple methodology to gain access to α,β-disubstituted conjugated enones from α-allenols in a sustainable metal catalysis context, considering the inexpensiveness and environmentally friendliness of iron(III) species and protons, has b
Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes
Itoh, Taisuke,Shimizu, Yohei,Kanai, Motomu
supporting information, p. 2736 - 2739 (2014/06/09)
A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
Synthesis and antimicrobial evaluation of some pyrazole derivatives
Sharshira, Essam Mohamed,Hamada, Nagwa Mohamed Mahrous
scheme or table, p. 4962 - 4971 (2012/09/22)
Reaction of a series of (E)-3-phenyl-4-(p-substituted phenyl)-3-buten-2- ones with p-sulfamylphenyl hydrazine in glacial acetic acid gave the corresponding hydrazones, subsequent treatment of which with 30% HCl afforded pyrazole-1-sulphonamides. On the ot
Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine
Zhang, Qian-Qian,Xie, Jian-Hua,Yang, Xiao-Hui,Xie, Jian-Bo,Zhou, Qi-Lin
supporting information, p. 6158 - 6161 (2013/02/23)
A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).
Addition of arylboronic acids to arylpropargyl alcohols en route to indenes and quinolines
Panteleev, Jane,Huang, Richard Y.,Lui, Erica K. J.,Lautens, Mark
supporting information; experimental part, p. 5314 - 5317 (2011/12/01)
A regio- and stereoselective rhodium-catalyzed synthesis of trisubstituted allylic alcohols is described. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.
Palladium-catalyzed oxidative cross-coupling reaction of arylboronic acids with diazoesters for stereoselective synthesis of (E)-α,β- diarylacrylates
Tsoi, Yuk-Tai,Zhou, Zhongyuan,Chan, Albert S. C.,Yu, Wing-Yiu
supporting information; experimental part, p. 4506 - 4509 (2010/12/25)
A Pd-catalyzed oxidative cross-coupling reaction of arylboronic acids with α-diazoesters was achieved using molecular oxygen as the sole reoxidant, and E-α,β-diarylacrylates were obtained in good yields and >20:1 E-to-Z selectivity.
CuH-catalyzed enantioselective 1,2-reductions of α,β-unsaturated ketones
Moser, Ralph,Boskovia, Zarko V.,Crowe, Christopher S.,Lipshutz, Bruce H.
supporting information; experimental part, p. 7852 - 7853 (2010/08/04)
The first study on a general technology for arriving at valued nonracemic allylic alcohols using asymmetric ligand-accelerated catalysis by copper hydride is described.
Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation
Lu, Sheng-Mei,Bolm, Carsten
supporting information; experimental part, p. 8920 - 8923 (2009/05/30)
(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.
