- Cu-Catalyzed cyanoalkylation of electron-deficient alkenes with unactivated alkyl bromides
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We here report the photoinduced Cu-catalyzed cyanoalkylation of electron-deficient alkenes by using alkyl bromides as alkylation reagents. In the reactions, 1°, 2°, and 3° unactivated alkyl bromides with various sensitive functional groups were well tolerated with good yields. Notably, terminal and internal alkenes, as well as alkene-containing peptides, were all tolerated well.
- Wang, Chao,Shang, Qinyu,Qi, Rupeng,Chai, Hongli,Wang, Hongying,Guo, Mengzhun,Xu, Zhaoqing
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supporting information
p. 9991 - 9994
(2019/08/22)
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- Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides
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2-Piperidinones are synthesized in a single step from imines and 2-cyano glutaric anhydrides. The reaction provides the products in good diastereoselectivity and generates a quaternary stereogenic center. Substitutions on the anhydride skeleton are well tolerated to provide 2-piperidinones with three stereogenic centers from a single transformation. The pertinent transition structures have also been computed using quantum mechanics and reveal the key interactions controlling the stereochemical outcome of the reaction.
- Di Maso, Michael J.,Snyder, Kevin M.,De Souza Fernandes, Fábio,Pattawong, Ommidala,Tan, Darlene Q.,Fettinger, James C.,Cheong, Paul Ha-Yeon,Shaw, Jared T.
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p. 4794 - 4801
(2016/04/05)
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- Base-catalysed intramolecular hydroamination of vinyl sulfiies
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Small amounts of n-butyllithium catalyse the highly efficient hydroamination of a large variety of vinyl sulfides. This novel methodology offers an easy access to a wide range of nitrogen heterocycles, including simple pyrrolidines and piperidines, as well as more complex bicyclic compounds. Subsequent transformations of the sulfur group led to the formation of functionalised alkaloid-like substructures. Wiley-VCH Verlag GmbH & Co. KGaA.
- Quinet, Coralie,Sampoux, Laetitia,Marko, Istvan E.
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supporting information; experimental part
p. 1806 - 1811
(2009/09/06)
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- Nickel complexes of nio-functionalized n-Heterocyclic carbenes as precatalysts for michael reactions in air at room temperature under the much preferred base-Free conditions
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A series of several new nickel precatalysts supported over N/O-functionalized N-heterocyclic carbenes (NHC) for the Michael reactions of B-dicarbonyl, B-keto ester, B-diester, and a-cyano ester compounds with a,B-unsaturated carbonyl compounds in air at ambient temperature under the much preferred base-free conditions are reported. Specifically, the nickel complexes, [1-(R1-aminocarbonylmethyl)-3-R2-imid-azol-2-ylidene]2Ni [R1 =2-C6H4(OMe); R2 = Me (1b), iPr (2b), CH2Ph (3b) and R1 = 2-CH2C4H3O; R2 =Me (4b), CH2Ph (5b)] carried out the highly convenient base-free Michael addition of the activated C-H compounds across a,B-unsaturated car- bonyl compounds in air at room temperature. The complexes 1b-5b were synthesized by the direct reaction of the respective imidazolium chloride salt with NiCl2-6H2Oin CH3CN in the presence of K2CO3 as a base. The exceptional stability of 1b-5b has been attributed to the deeply buried nickel-NHC CT-bonding molecular orbitals as evidenced from the density functional theory (DFT) studies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.
- Ray, Sriparna,Shaikh, Mobin M.,Ghosh, Prasenjit
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experimental part
p. 1932 - 1941
(2009/10/30)
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- Use of condensed pyrimidine derivatives for the treatment of autoimmune and inflammatory diseases
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The invention relates to the use of a compound of the formula I, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for use in modulating an immune or inflammatory response: wherein: Z = O or S; n = 1-3; R3 = -CO2R8, -C(O)SR8, -C(O)NHR8, -C(S)OR8, -C(S)SR8, -C(S)NHR8, -C(NH)SR8 or -C(NH)NHR8, wherein R8 is -H or alkyl; R4 = -H, -CH2R5 or -CH2CH2R5, wherein R5 independently has one of the meanings of R3; B = -NR2-, -CH2NR2-, -CH2CH2NR2-, -CH2CHR7- or -CH2O-, wherein R2 is H or a C1-3 alkyl, alkenyl or alkynyl group, and R7 is H or a C1-3 alkyl or alkoxy group; A = wherein R1 = -NH2 or -OH, C and D are each, independently, a 5- or 6-membered, substituted or unsubstituted, aromatic or non-aromatic ring which may also contain one or more heteroatoms, and C is connected to group B in any available position.
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Page/Page column 10; 19
(2008/12/07)
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- Binary caesium-lanthanum oxide supported on MCM-41: A new stable heterogeneous basic catalyst
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Heterogeneous mesoporous stable basic catalysts have been prepared by wet or solid-state impregnation of MCM-41 with caesium acetate and lanthanum nitrate followed by thermal decomposition. 133Cs MAS NMR data of CsLa/MCM-41 show an increase in
- Kloetstra,Van Laren,Van Bekkum
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p. 1211 - 1220
(2007/10/03)
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- SYNTHESIS OF POLYFUNCTIONAL ALIPHATIC CARBONYL COMPOUNDS UNDER PHASE-TRANSFER CONDITIONS
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We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and β-halopropionic acids and addition of the CH acids mentioned and their analogues to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products.We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the synthesis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.
- Sizov, A. Yu.,Dombrovskii, V. A.,Yanovskaya, L. A.
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p. 955 - 961
(2007/10/02)
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- One-Pot Synthesis of cis Fixed β-Diketones of Bicycloalkanes, 2
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Starting from 2-cycloalken-1-ones 1 the substituted cis fixed β-diketones of bicycloalkanes 4 have been obtained by a combined Michael addition of α,α,ω-alkanetricarboxylates (and related species) 2 and Dieckmann cyclization of the intermediates 3.Reactions of the β-diketone system as well as modifications of the disubstituted malonate system of 4 are reported.
- Schank, Kurt,Lorig, Werner
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p. 112 - 136
(2007/10/02)
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