139474-72-9Relevant academic research and scientific papers
Potassium fluoride/basic alumina as far superior heterogeneous catalyst for the chemoselective conjugate addition of nitroalkanes to electron-poor alkenes having two electron-withdrawing groups in α- and β-positions
Ballini, Roberto,Palmieri, Alessandro
, p. 1154 - 1156 (2006)
The chemoselective, conjugate addition of nitroalkanes to electron-poor alkenes, with two electron-withdrawing groups in the α- and β-positions, can be easily performed at room temperature under solventless conditions using potassium fluoride/basic alumin
Michael Addition of Nitroalkanes to Dimethyl Maleate with DBU. A New Direct Method for the Synthesis of Polyfunctionalized α,β-Unsaturated Esters.
Ballini, Roberto,Rinaldi, Alessandro
, p. 9247 - 9250 (1994)
Michael addition of nitroalkanes to dimethyl maleate, in acetonitrile and with 1,8-diazabicycloundec-7-ene (DBU) as base affords, directly, polyfunctionalized α,β-unsaturated esters, via elimination of nitrous acid.
Nitroalkanes as alkyl anion synthons - A new approach to the synthesis of 2-substituted N-ethyl succinimides and 2-substituted succinate diesters via nitroalkanes
Ballini, Roberto,Bosica, Giovanna
, p. 2087 - 2089 (1996)
2-Substituted N-ethyl succinimide and 2-substituted succinate diesters were obtained by two key steps: (i) Michael addition of a nitroalkane to the appropriate enedione derivative under basic conditions (DBU), with the concomitant elimination of nitrous acid, and (ii) selective reduction of the obtained enone with nickel boride, in methanol/THF. In this context the nitroalkane acts as an alkyl anion synthon. By this method trimethyl tricarboxylates were also synthesized. VCH Verlagsgesellschaft mbH, 1996.
Regioselective monoalkylation of dimethyl alkylidenesuccinates: Simple approach to dialkyl-substituted maleic anhydrides including chaetomellic acid A
Kshirsagar, Umesh A.,Argade, Narshinha P.
experimental part, p. 1804 - 1808 (2011/07/29)
Natural and nonnatural dialkylmaleic anhydrides were readily prepared from dimethyl alkylidenesuccinates by sodium hexamethyldisilazide-induced selective monoalkylation followed by base-catalyzed hydrolysis. Georg Thieme Verlag Stuttgart - New York.
Synthesis of versatile building blocks through asymmetric hydrogenation of functionalized itaconic acid mono-esters
Hekking, Koen F. W.,Lefort, Laurent,De Vries, Andre H. M.,Van Delft, Floris L.,Schoemaker, Hans E.,De Vries, Johannes G.,Rutjes, Floris P. J. T.
experimental part, p. 85 - 94 (2009/04/07)
The rhodium-catalyzed asymmetric hydrogenation of several β-substituted itaconic acid monoesters, using a library of monodentate phosphoramidite and phosphite ligands is described. Two β-alkylsubstituted substrates were readily hydrogenated by the rhodium complex Rh(COD) 2BF4 in combination with (S)-PipPhos as a ligand resulting in ees of 99 %. In contrast, the corresponding more hindered β-arylsubstituted substrates did not exhibit acceptable enantioselectivities under these conditions. However, the use of a 48-membered ligand library led to the identification of several suitable ligands for these substrates, resulting in ees of 89-99%. The resulting optically active succinic acid derivatives are potentially useful building blocks for more elaborate compounds, because of the ability to differentiate between the carboxylic acid and the ester groups on either side of the molecule.
Catalytic asymmetric alkynylation and arylation of aldehydes by an H 8-binaphthyl-based amino alcohol ligand
Ruan, Jiwu,Lu, Gui,Xu, Lijing,Li, Yue-Ming,Chan, Albert S. C.
experimental part, p. 76 - 84 (2009/04/11)
A novel chiral H8-1,1'-binaphthyl-based amino alcohol ligand (1Ra,2S,3R)-2 has been synthesized and applied in the direct nucleophilic addition of organozincs (alkynylzinc and arylzinc prepared in situ) to aldehydes, yielding the corresponding optically active propargylic alcohols and diarylmethanols in high yields and good to excellent enantioselectivities. For the asymmetric arylation reaction, one catalyst (1Ra,2S,3R)-2 can afford both enantiomers of many pharmaceutically interesting diarylmethanols by a proper combination of various arylzinc reagents and aldehydes.
Nitroalkanes and dimethyl maleate as source of 3-alkyl succinic anhydrides and (E)-3-alkylidene succinic anhydrides
Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis,Righi, Paolo
, p. 681 - 685 (2007/10/03)
Nitroalkanes react with dimethyl maleate giving a tandem Michael addition/elimination of nitrous acid. The obtained (E)-2-alkylidene dimethyl succinates are: (i) reduced to the corresponding 2-alkyl dimethyl succinates which after hydrolysis produce 1,4-dicarboxylic acids that are prone to convert into the corresponding 3-alkyl succinic anhydrides or (ii) hydrolysed to (E)-2-alkylidene-succinic acids that are easily cyclised to (E)-3-alkylidene succinic anhydrides.
Synthesis of (E)-3-alkylidenepyrrolidines by nucleophilic ring closure of (E)-2-alkylidene-1,4-diol derivatives
Ballini, Roberto,Bosica, Giovanna,Mase?, Aldo,Petrini, Marino
, p. 2927 - 2931 (2007/10/03)
The synthesis of N-protected (E)-3-alkylidenepyrrolidines is reported. Nitroalkanes react with unsaturated 1,4-diesters and 1,4-keto esters, giving a tandem Michael addition/elimination of nitrous acid. The obtained 1,4-dicarbonyl compounds are reduced to the corresponding diols and then converted into their mesylates. Reaction of mesylates with benzylamine or 4-methylbenzenesulfonylamide affords the unsaturated pyrrolidines. Use of the sulfonylamide for the cyclization step has advantages over that of benzylamine, since it gives better yields of pyrrolidines, and furthermore, the benzenesulfonyl group can be efficiently removed in the presence of unsaturated bonds.
