- Chiral indole compounds and preparation method thereof
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The invention discloses chiral indole compounds and a preparation method thereof. Cyclobutanone compounds with iodine-substituted benzene ring ortho-positions and aryl sulfonamide compounds with acetenyl-substituted benzene ring ortho-positions are used a
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Paragraph 0046-0047
(2021/02/06)
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- Enantioselective Cross-Exchange between C?I and C?C σ Bonds
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A palladium-catalyzed enantioselective intramolecular σ-bond cross-exchange between C?I and C?C bonds is realized, providing chiral indanones bearing an alkyl iodide group and an all-carbon quaternary stereocenter. Pd/TADDOL-derived phosphoramidite is found to be an efficient catalytic system for both C?C bond cleavage and alkyl iodide reductive elimination. In addition to aryl iodides, aryl bromides can also be used for this transformation in the presence of KI. Density-functional theory (DFT) calculation studies support the ring-opening of cyclobutanones occuring through an oxidative addition/reductive elimination process involving PdIV species.
- Sun, Yu-Li,Wang, Xing-Ben,Sun, Feng-Na,Chen, Qian-Qian,Cao, Jian,Xu, Zheng,Xu, Li-Wen
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supporting information
p. 6747 - 6751
(2019/04/26)
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- Taming Silylium Ions for Synthesis: N-Heterocycle Synthesis via Stereoselective C-C Bond Formation
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Silylium ions (formally [R 3 Si] +) have long been the subject of investigations and significant debate in both theoretical and experimental chemistry, but few catalytic, synthetic applications have been reported due to the exception
- Moyer, Brandon S.,Gagné, Michel R.
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supporting information
p. 2429 - 2434
(2017/10/06)
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- Preparation and catalytic performance of a molecularly imprinted Pd complex catalyst for Suzuki cross-coupling reactions
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A SiO2-supported molecularly imprinted Pd complex with SiO2-matrix overlayers was prepared as a Suzuki cross-coupling catalyst. A ligand on the supported Pd complex was used as a molecular imprinting template to create the reaction space. The structures of the supported and molecularly imprinted Pd complexes on SiO2 were determined by solid-state MAS 13C, 29Si, and 31P NMR; diffuse reflectance UV/vis; XPS; and Pd K-edge XAFS. The catalytic performance of the molecularly imprinted Pd complex catalyst was very different for various combinations of aryl iodides and arylboronic acids. Reactants with bulky substituent groups were hindered on the imprinted catalyst in Suzuki cross-coupling reactions.
- Muratsugu, Satoshi,Maity, Niladri,Baba, Hiroshi,Tasaki, Masahiro,Tada, Mizuki
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supporting information
p. 3125 - 3134
(2017/03/15)
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- Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons
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A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.
- Ma, Weiwei,Fang, Jie,Ren, Jun,Wang, Zhongwen
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supporting information
p. 4180 - 4183
(2015/09/15)
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- Diisobutylaluminum hydride promoted cyclization of o -(trimethylsilylethynyl)styrenes to indenes
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The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerizati
- Kinoshita, Hidenori,Hirai, Nobuyoshi,Miura, Katsukiyo
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p. 8171 - 8181
(2015/03/18)
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- Dihydrobiphenylenes through ruthenium-catalyzed [2+2+2] cycloadditions of ortho-alkenylarylacetylenes with alkynes
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A new synthetic route to dihydrobiphenylenes has been developed. The process involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. Mechanistic aspects of this [2+2+2] cycloaddition are discussed. A new synthetic route to dihydrobiphenylenes involves a mild RuII-catalyzed [2+2+2] dimerization of ortho-alkenylarylacetylenes or its more versatile variant, the Ru-catalyzed [2+2+2] cycloaddition of ortho-ethynylstyrenes with alkynes. The mechanistic aspects of this [2+2+2] cycloaddition are also discussed. Copyright
- Garcia-Rubin, Silvia,Gonzalez-Rodriguez, Carlos,Garcia-Yebra, Cristina,Varela, Jesus A.,Esteruelas, Miguel A.,Saa, Carlos
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supporting information
p. 1841 - 1844
(2014/03/21)
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- A conjunctive carboiodination: Indenes by a double carbopalladation- reductive elimination domino process
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Something gained, nothing lost: A Pd0-catalyzed domino intermolecular/intramolecular process terminated by carbohalogenation is reported. In this reaction, two new C-C bonds, one new C-I bond and one five-membered ring are formed in a single step, and all of the atoms in the starting materials are incorporated into the product (see scheme). Copyright
- Jia, Xiaodong,Petrone, David A.,Lautens, Mark
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supporting information
p. 9870 - 9872
(2012/10/30)
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- Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
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A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
- Serra, Stefano
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experimental part
p. 619 - 628
(2011/07/08)
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- Non-catalytic conversion of C-F bonds of benzotrifluorides to C-C bonds using organoaluminium reagents
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A facile method for the conversion of C-F bonds of benzotrifluorides to C-C bonds has been developed using aluminium reagents in the absence of catalysts.
- Terao, Jun,Nakamura, Misaki,Kambe, Nobuaki
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scheme or table
p. 6011 - 6013
(2010/11/16)
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