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1.
The first addition-elimination of nitroalkanes to 3-phenacylideneoxindoles was developed, affording the corresponding 3-alkenylphenacylidene-oxindoles with high yields.The addition-elimination mechanism of 3-phenacylideneoxindoles with nitroalkanes and removable NO2 group in concert guarantees the high regioselectivity. 相似文献
2.
A simple synthetic route to 1-p-methoxyphenyl and 1-p-methoxyphenyl-4-methylbicyclo [2.2.1]heptan-7-one 6b,a has been developed through benzilic acid rearrangement of the bicyclo[2.2.1]octandiones 2b,a. The oxidation of 7-hydroxy-1-p-methoxyphenyl-4-methylbicyclo[2.2.1]heptan-7-carboxylic acid 3a with lead tetraacetate gives the carbolactone 7a which is also formed by the reaction of the ketone 6a with m-chloroperbenzoic acid. 相似文献
3.
Highly Diastereo‐ and Enantioselective Michael Addition of Nitroalkanes to 2‐Enoyl‐Pyridine N‐Oxides Catalyzed by Scandium(III)/Copper(II) Complexes
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Lijun Li Sheng Zhang Yanbin Hu Yanan Li Chong Li Prof. Zhenggen Zha Prof. Dr. Zhiyong Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(37):12885-12888
A C2‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro‐2H‐pyrrol 4 a . Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design. 相似文献
4.
Manzano R Andrés JM Álvarez R Muruzábal MD de Lera ÁR Pedrosa R 《Chemistry (Weinheim an der Bergstrasse, Germany)》2011,17(21):5931-5938
A series of chiral thioureas derived from easily available diamines, prepared from α-amino acids, have been tested as catalysts in the enantioselective Michael additions of nitroalkanes to α,β-unsaturated ketones. The best results are obtained with the bifunctional catalyst prepared from L-valine. This thiourea promotes the reaction with high enantioselectivities and chemical yields for aryl/vinyl ketones, but the enantiomeric ratio for alkyl/vinyl derivatives is very modest. The addition of substituted nitromethanes led to the corresponding adducts with excellent enantioselectivity but very poor diastereoselectivity. Evidence for the isomerization of the addition products has been obtained from the reaction of chalcone with [D(3)]nitromethane, which shows that the final addition products epimerize under the reaction conditions. The epimerization explains the low diastereoselectivity observed in the formation of adducts with two adjacent tertiary stereocenters. Density functional studies of the transition structures corresponding to two alternative activation modes of the nitroalkanes and α,β-unsaturated ketones by the bifunctional organocatalyst have been carried out at the B3LYP/3-21G* level. The computations are consistent with a reaction model involving the Michael addition of the thiourea-activated nitronate to the ketone activated by the protonated amine of the organocatalyst. The enantioselectivities predicted by the computations are consistent with the experimental values obtained for aryl- and alkyl-substituted α,β-unsaturated ketones. 相似文献
5.
Alexander V. Aksenov Igor Yu. Grishin Nicolai A. Aksenov Vladimir V. Malyuga Dmitrii A. Aksenov Mezvah A. Nobi Michael Rubin 《Molecules (Basel, Switzerland)》2021,26(14)
Nitroalkanes activated with polyphosphoric acid serve as efficient electrophiles in reactions with various nucleophilic amines. Strategically placed second functionality allows for the design of annulation reactions enabling preparation of various heterocycles. This strategy was employed to develop an innovative synthetic approach towards 3,4-dihydroquinazolines from readily available 2-(aminomethyl)anilines. 相似文献
6.
Alexander V. Aksenov Nikita K. Kirilov Nicolai A. Aksenov Dmitrii A. Aksenov Elena A. Sorokina Carolyn Lower Michael Rubin 《Molecules (Basel, Switzerland)》2021,26(18)
Nitroalkanes activated with polyphosphoric acid could serve as efficient electrophiles in reactions with amines and hydrazines, enabling various cascade transformations toward heterocyclic systems. This strategy was developed for an innovative synthetic protocol employing simultaneous or sequential annulation of two different heterocyclic cores, affording [1,2,4]triazolo[4,3-a]quinolines with 1,3,4-oxadiazole substituents. 相似文献
7.
Roberto Ballini Dennis FioriniMaria Victoria Gil Alessandro Palmieri 《Tetrahedron letters》2003,44(50):9033-9034
The reaction of nitroalkanes with 2-chloro-3-phenylsulfonylpropanenitrile, in the presence of three equivalents of DBU at −10°C, allows the synthesis of polyfunctionalized α,β-unsaturated nitriles. The method proceeds through three different reactions carried out in a tandem sequence, allowing the one-pot formation of the α,β-unsaturated nitriles, generally, with complete E stereochemistry. 相似文献
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9.
Alumina for chromatography (acidic, basic and neutral), magnesia and sodium-doped magnesia calcined at 350, 450, 550, 650
and 750oC for 4 h were used as solid bases to catalyze the synthesis of 1-nitro-2-butanol from nitromethane and propionaldehyde (Henry
reaction).
This revised version was published online in June 2006 with corrections to the Cover Date. 相似文献
10.