- An alternative to the Swern oxidation
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A variety of alcohols have been oxidized under mild conditions by the DMSO-Ph3P·X2 complexes. The reaction does not produce any Pummerer product. A mechanism for the reaction is proposed.
- Bisai, Alakesh,Chandrasekhar,Singh, Vinod K.
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Read Online
- Synthetic applications of the amine-base treatment in the ozonolysis of substituted-allyl silyl ethers or -allyl esters via a novel ene-diol type rearrangement
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The ozonolysis of substituted-allyl silyl ethers or -allyl esters followed by treatment with bases gave the corresponding α-silyloxy ketones or α-acyloxy ketones in good yields. The reaction is proposed to proceed via a novel ene-diol rearrangement of the corresponding α-silyloxy aldehydes or α-acyloxy aldehydes intermediates.
- Hon, Yung-Son,Wong, Ying-Chieh
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Read Online
- Cobalt-Catalyzed Reductive C-O Bond Cleavage of Lignin β-O-4 Ketone Models via in Situ Generation of the Cobalt-Boryl Species
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An efficient and mild method for reductive C-O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation involves steps of carbonyl insertion, 1,2-Brook type rearrangement, β-oxygen elimination, and rate-limiting regeneration of the catalytic active Co-B species.
- Gao, Kecheng,Xu, Man,Cai, Cheng,Ding, Yanghao,Chen, Jianhui,Liu, Bosheng,Xia, Yuanzhi
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supporting information
p. 6055 - 6060
(2020/08/12)
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- Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole
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A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.
- Dai, Haican,Yu, Sisi,Cheng, Wanli,Xu, Ze-Feng,Li, Chuan-Ying
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supporting information
p. 6417 - 6420
(2017/07/10)
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- Green organocatalytic α-hydroxylation of ketones
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An efficient and green method for the α-hydroxylation of substituted ketones has been developed. This method includes the in situ conversion of various ketones into the corresponding silyl enol ethers and their oxidation to the corresponding α-hydroxy ketones. Two protocols have been established leading either to protected α-hydroxy carbonyls or free α-hydroxy ketones. Both procedures are easy to follow and lead to good to high yields for a variety of ketones.
- Voutyritsa, Errika,Theodorou, Alexis,Kokotos, Christoforos G.
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p. 5708 - 5713
(2016/07/06)
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- SPIRO-THIAZOLONES
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The present invention provides spiro-thiazolones, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The present compounds are useful as therapeutics acting peripherally and centrally in the conditions of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.
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Page/Page column 77
(2016/06/06)
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- Identification of a 4-(hydroxymethyl)diarylhydantoin as a selective androgen receptor modulator
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Structural modification performed on a 4-methyl-4-(4-hydroxyphenyl) hydantoin series is described which resulted in the development of a new series of 4-(hydroxymethyl)diarylhydantoin analogues as potent, partial agonists of the human androgen receptor. T
- Nique, Francois,Hebbe, Severine,Triballeau, Nicolas,Peixoto, Christophe,Lefrancois, Jean-Michel,Jary, Helene,Alvey, Luke,Manioc, Murielle,Housseman, Christopher,Klaassen, Hugo,Van Beeck, Kris,Guedin, Denis,Namour, Florence,Minet, Dominque,Van Der Aar, Ellen,Feyen, Jean,Fletcher, Stephen,Blanque, Roland,Robin-Jagerschmidt, Catherine,Deprez, Pierre
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supporting information
p. 8236 - 8247,12
(2020/09/15)
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- PYRIMIDONE DERIVATIVES USED AS TAU PROTEIN KINASE 1 INHIBITORS
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A compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: wherein Z represents nitrogen atom or C-X; X represents hydrogen atom or fluorine atom; R1 is hydrogen atom or a C1 -C3 alkyl group; L represents single bond or a C1 -C6 alkylene group which may be substituted; Y represents single bond, sulfur atom, oxygen atom, NH, or the like; R2 represents hydrogen atom or a cyclic group which may be substituted, which is used for preventive and/or therapeutic treatment of a disease caused by abnormal activity of tau protein kinase 1 such as a neurodegenerative diseases (e.g. Alzheimer disease).
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Page/Page column 42
(2011/02/24)
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- SELECTIVE HYDROXAMIC ACID BASED MMP-12 AND MMP-13 INHIBITORS
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The present invention provides a compound of formula (I) said compound is inhibitor of MMP-12 and/or MMP-13, and thus can be employed for the treatment of a disorder or disease characterized by abnormal activity of MMP-12 and/ or MMP- 13. Accordingly, the compound of formula (I) can be used in treatment of disorders or diseases mediated by MMP-12 and/or MMP-13. Finally, the present invention also provides pharmaceutical composition that include the compound of formula (I).
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Page/Page column 37
(2010/04/03)
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- A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates
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The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.
- Hon, Yung-Son,Wong, Ying-Chieh,Wu, Kuo-Jui
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experimental part
p. 896 - 914
(2009/12/06)
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- Biomimetic transfer hydrogenation of 2-alkoxy- and 2-aryloxyketones with iron-porphyrin catalysts
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In situ generated iron porphyrins are applied as homogeneous catalysts in the transfer hydrogenation of α-substituted ketones. Using 2-propanol as hydrogen donor various protected 1,2-hydroxyketones are reduced to the corresponding mono-substituted 1,2-di
- Enthaler, Stephan,Spilker, Bj?rn,Erre, Giulia,Junge, Kathrin,Tse, Man Kin,Beller, Matthias
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p. 3867 - 3876
(2008/09/20)
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- Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation
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Aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. On contrary, α-silyloxy aldehydes give α-silyloxy ketones via Oppenauer oxidation under similar condition. Tishchenko reaction of ω-alkene aldehydes followed by RCM and hydrogenation affords a convenient method to prepare the 11-37 membered macrocyclic lactones.
- Hon, Yung-Son,Wong, Ying-Chieh,Chang, Chun-Ping,Hsieh, Cheng-Han
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p. 11325 - 11340
(2008/03/12)
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- Synthesis of 3-fluorofuran-2(5H)-ones based on Z/E photoisomerisation and cyclisation of 2-fluoro-4-hydroxybut-2-enoates
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Mixtures of some (E)- and (Z)-2-fluoroalk-2-enoates prepared from the corresponding 2-hydroxycarbonyl compounds and ethyl 2-(diethoxyphosphoryl)-2- fluoroacetate have been transformed in high conversions into the target 3-fluorofuran-2(5H)-ones by an effi
- Pomeisl, Karel,Cejka, Jan,Kvicala, Jaroslav,Paleta, Oldrich
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p. 5917 - 5925
(2008/04/13)
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- Synthesis and DNA cleavage reaction characteristics of enediyne prodrugs activated via an allylic rearrangement by base or UV irradiation
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A number of enediyne prodrugs 1-5 possessing an (E)-3-hydroxy-4-(2′- hydroxy-1′-phenylethylidene)cyclodeca-1,5-diyne scaffold have been synthesized via the Sonogashira coupling and an intramolecular Nozaki-Hiyama-Kishi reaction as the key steps. Upon incu
- Tachi, Yukihiro,Dai, Wei-Min,Tanabe, Kazuhito,Nishimoto, Sei-Ichi
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p. 3199 - 3209
(2007/10/03)
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- Development and comparison of the substrate scope of Pd-catalysts for the aerobic oxidation of alcohols
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(Chemical Equation Presented) Three catalysts for aerobic oxidation of alcohols are discussed and the effectiveness of each is evaluated for allylic, benzylic, aliphatic, and functionalized alcohols. Additionally, chiral nonracemic substrates as well as chemoselective and diastereoselective oxidations are investigated. In this study, the most convenient system for the Pd-catalyzed aerobic oxidation of alcohols is Pd(OAc)2 in combination with triethylamine. This system functions effectively for the majority of alcohols tested and uses mild conditions (3 to 5 mol % of catalyst, room temperature). Pd(IiPr)(OAc)2(H2O) (1) also successfully oxidizes the majority of alcohols evaluated. This system has the advantage of significantly lowering catalyst loadings but requires higher temperatures (0.1 to 1 mol % of catalyst, 60°C). A new catalyst is also disclosed, Pd(IiPr)(OPiv)2 (2). This catalyst operates under very mild conditions (1 mol %, room temperature, and air as the O2 source) but with a more limited substrate scope.
- Schultz, Mitchell J.,Hamilton, Steven S.,Jensen, David R.,Sigman, Matthew S.
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p. 3343 - 3352
(2007/10/03)
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- Novel synthesis of 4′C-aryl-branched acyclic nucleoside using [3,3]-sigmatropic rearrangement
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A very efficient synthetic route for preparing a novel 4′-C-aryl branched-1′,2′-seco-2′,3′-dideoxy-2′, 3′-didehydro-nucleoside is described. Mesylate 7 was successfully synthesized via a Horner-Wadsworth-Emmons reaction and a [3,3]-sigmatropic rearrangeme
- Baik, Gun Ha,Chung, Bong Young,Oh, Chang-Hyun,Cho, Jung-Hyuck,Ko, Ok Hyun,Hong, Joon Hee
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p. 1781 - 1788
(2007/10/03)
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- Oxygenation of Silyl Enol Ethers and Silyl Ketene Acetals with Molecular Oxygen and Aldehyde Catalyzed by Nickel(II) Complex. A Convenient Method for the Preparation of α-Hydroxy Carbonyl Compounds
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In the presence of a catalytic amount of nickel(II) complex, silyl enol ethers and silyl ketene acetals are smoothly oxygenated by the combined use of molecular oxygen and aldehyde to afford α-siloxy carbonyl compounds via possible intermediates, siloxy epoxides.And on treatment of the α-siloxy carbonyl compounds with potassium fluoride α-hydroxy carbonyl compounds are obtained in good to high yields.
- Takai, Toshihiro,Yamada, Tohru,Rhode, Oliver,Mukaiyama, Teruaki
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p. 281 - 284
(2007/10/02)
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