131323-45-0Relevant articles and documents
Ruthenium-Catalyzed Allylation of Primary Alcohols by Allylic Acetates: A Novel Synthesis of α,β-Unsaturated Ketones
Kondo, Teruyuki,Mukai, Takeshi,Watanabe, Yoshihisa
, p. 487 - 489 (1991)
Certain ruthenium complexes show high catalytic activity in the synthesis of α,β-unsaturated ketones from primary alcohols and allylic acetates.Here, ?-allylruthenium intermediates apparently operate as nucleophiles rather than as electrophiles.
Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis
Erkman, Kristin,J?rving, Ivar,K?ster, Kristjan,Kanger, T?nis,Leito, Ivo,Mart?nova, Jevgenija,Metsala, Andrus,Saame, Jaan,Trubits?n, Dmitri
, p. 1047 - 1059 (2020/04/01)
An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium
Chen, Zhili,Hu, Fangli,Huang, Shengli,Zhao, Zhengxing,Mao, Hui,Qin, Wenling
, p. 8100 - 8111 (2019/06/17)
Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
Decarboxylative allylation of arylglyoxylic acids with allyl alcohol
Grünberg, Matthias F.,Goo?en, Lukas J.
, p. 140 - 143 (2013/10/01)
A decarboxylative allylation of arylglyoxylic acids with allyl alcohol has been developed. In the presence of catalytic amounts of Pd(dba) 2 and PPh3, the substrates are in an esterification equilibrium with the allyl arylglyoxylates, which are continuously decarboxylated to give α,β-unsaturated ketones along with CO2 and water as the only byproducts.
Decarboxylative allylation of glyoxylic acids with diallyl carbonate
Manjolinho, Filipe,Gruenberg, Matthias F.,Rodriguez, Nuria,Goossen, Lukas J.
supporting information; experimental part, p. 4680 - 4683 (2012/10/08)
A catalyst system consisting of Pd(PPh3)4 and P(pTol)3 was found to effectively promote the intermolecular decarboxylative coupling of α-oxocarboxylic acids with diallyl carbonate to give α,β-unsaturated ketones. The key advantage of the new reaction protocol is that preformation of the allyl esters is not required. The reaction is believed to proceed via phosphane-mediated decarboxylation of the α-oxocarboxylates, leading to acyl anion equivalents that are allylated within the coordination sphere of the palladium catalyst. Under the reaction conditions, the double bond then migrates into conjugation with the carbonyl group. Copyright
Synthesis of α,β-unsaturated ketones by Pd-catalyzed decarboxylative allylation of α-oxocarboxylates
Rodriguez, Nuria,Manjolinho, Filipe,Gruenberg, Matthias F.,Goossen, Lukas J.
supporting information; experimental part, p. 13688 - 13691 (2012/01/15)
A palladium/p-tolylphosphine system has been developed that catalyzes the extrusion of carbon dioxide from α-oxocarboxylic acid allyl esters, leading to α,β-unsaturated ketones (see scheme). The palladium complex activates the substrate and mediates the carbon-carbon bond formation to give allyl ketones, and subsequent double bond shift to the α,β position. The actual decarboxylation step with formation of the acyl nucleophile is promoted by phosphine.
A new paradigm for carbon-carbon bond formation: Aerobic, copper-templated cross-coupling
Villalobos, Janette M.,Srogl, Jiri,Liebeskind, Lanny S.
, p. 15734 - 15735 (2008/09/20)
Thiol esters and boronic acids react to produce ketones under aerobic conditions in the presence of catalytic quantities of a CuI or CuII salt. The reaction occurs at reasonable rates between room temperature and 50 °C at neutral pH using thiol esters derived from bulky 2° amides of thiosalicylamides such as those based on N-tert-butyl-2-mercaptobenzamide. In this mechanistically unprecedented reaction system, the carbon-carbon bond formation occurs through templating of the thiol ester and the boronic acid at copper; the system is rendered catalytic in copper under the aerobic conditions. Copyright
