cas 1813-94-1, ETHYL 4-FLUOROBENZOYLFORMATE

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Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters
Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re
Chen, Liang,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wen, Ziyang,Yang, Fan,Yang, Guichun
p. 2168 - 2171
(2022/02/17)

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters
By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.
Chu, Changhu,Dong, Wenwen,Lin, Jia,Teng, Jiangge,Wang, Zhiwei,Zhao, Rong
p. 6120 - 6126
(2021/07/21)

Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, o-Quinone Methides, and Dialkyl Phosphites
A highly regio- and diastereoselective approach for the synthesis of phosphate substituted dihydrocoumarins via Br?nsted base catalyzed [1,2]-phospha-Brook rearrangement is reported. The two-step, one-pot Michael addition of α-phosphonyloxy enolates proceeds by coupling of dialkyl phosphite and α-ketoesters to o-quinone methides, followed by an intramolecular cyclization, providing 3,4-dihydrocoumarin frameworks.
Kaur, Ravneet,Singh, Dipak,Singh, Ravi P.
p. 15702 - 15711
(2021/11/01)

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters
A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.
Luo, Xianglin,He, Runfa,Liu, Qiang,Gao, Yanping,Li, Jingqing,Chen, Xiuwen,Zhu, Zhongzhi,Huang, Yubing,Li, Yibiao
p. 5220 - 5230
(2020/05/18)

Green preparation method of aryl [alpha]-keto ester compound
The invention discloses a green preparation method of an aryl [alpha]-keto ester compound. The method comprises the specific steps that an [alpha]-diazo compound serves as a reaction raw material, copper sulfate serves as a catalyst, water serves as a solvent, a target product aryl [alpha]-keto ester compound is prepared through a reaction at the temperature of 60 DEG C, the structural general formula of the [alpha]-diazo compound is shown in the specification, and the structural general formula of the correspondingly prepared target product aryl [alpha]-keto ester compound is shown in the specification. The method for synthesizing the target product aryl [alpha]-keto ester compound by catalyzing the [alpha]-diazo compound derivative with copper sulfate has the advantages that the reactioncondition is green and mild, the catalyst is cheap and easy to obtain, the operation is simple and convenient, the yield is relatively high, the universality of a reaction substrate is wide, and thelike.
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Paragraph 0057-0060

(2020/05/30)

Copper(I)-catalyzed aerobic oxidation of α-diazoesters
A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.
Xu, Changming,Bai, Lei,Wang, Yongchang
p. 12579 - 12584
(2020/11/09)

Novel quinoline derivative inhibitor
The invention provides a novel quinoline derivative inhibitor, which has a structure represented by the following general formula (I). According to the invention, the compound provided by the invention can selectively inhibit tyrosine kinase TAM family/an
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Paragraph 0967; 0978-0980; 1000; 1011-1013

(2020/03/12)

Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade
A novel P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones has been developed that affords a facile synthesis of functionalized pyrrolidines in moderate to excellent yields with exclusive chemoselectivity and high diastereoselectivity. Mechanistic investigation reveals that the reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade. The reaction herein also represents the first study of the reactivity patterns of the Kukhtin-Ramirez adducts toward ambiphilic nucleophile-electrophiles.
Liu, Rongfang,Liu, Jialin,Cao, Jilei,Li, Ruifeng,Zhou, Rong,Qiao, Yan,Gao, Wen-Chao
supporting information
p. 6922 - 6926
(2020/09/15)

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters
The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.
Ni, Ke,Meng, Ling-Guo,Ruan, Hongjie,Wang, Lei
supporting information
p. 8438 - 8441
(2019/07/22)

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization
Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.
Yang, Qi-Liang,Xing, Yi-Kang,Wang, Xiang-Yang,Ma, Hong-Xing,Weng, Xin-Jun,Yang, Xiang,Guo, Hai-Ming,Mei, Tian-Sheng
supporting information
p. 18970 - 18976
(2019/12/04)

Template-Directed Synthesis of Photocatalyst-Encapsulating Metal-Organic Frameworks with Boosted Photocatalytic Activity
In the past decade, the use of visible light to promote organic transformations has gained intense attention. In this study, we developed a template-directed synthesis method to use homogeneous Ru and Ir photocatalysts as structure-directing templates and succeeded to prepare a series of photocatalyst-encapsulating metal-organic frameworks (photocatalyst@MOFs) with zeolite-like structures. The open channels and polyhedral cages of MOFs effectively dispersed the encapsulated photocatalysts and facilitated the transport of reactants and products, leading to boosted catalytic activity and good reusability toward important organic reactions such as aerobic oxidation reaction of benzyl halides and the cyclization of tertiary anilines and maleimides under visible light. Moreover, we also demonstrate the versatility and universality of our templating strategy. It not only can form MOFs which cannot be accessed by other synthesis methods, but also can encapsulate various commercially available homogeneous photocatalysts into MOFs. This work explores an avenue to prepare heterogeneous photocatalysts to catalyze value-added reactions.
Yang, Xiaojie,Liang, Tao,Sun, Jiaxing,Zaworotko, Michael J.,Chen, Yao,Cheng, Peng,Zhang, Zhenjie
p. 7486 - 7493
(2019/08/26)

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis
The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.
Yu, Qing,Zhang, Yating,Wan, Jie-Ping
supporting information
p. 3436 - 3441
(2019/06/24)

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase
Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.
Xu, Jian,Peng, Yongzhen,Wang, Zhiguo,Hu, Yujing,Fan, Jiajie,Zheng, He,Lin, Xianfu,Wu, Qi
supporting information
p. 14499 - 14503
(2019/09/17)

Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group
Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB1 receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.
Tian, Duanshuai,Li, Chengxi,Gu, Guoxian,Peng, Henian,Zhang, Xumu,Tang, Wenjun
supporting information
p. 7176 - 7180
(2018/05/29)

Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers
The synthesis of chiral fluorine containing motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation of readily available vinyl fluorides. Various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups were found to be compatible with the reaction and provide the highly desirable product as single diastereomers with excellent enantioselectivities.
Ponra, Sudipta,Rabten, Wangchuk,Yang, Jianping,Wu, Haibo,Kerdphon, Sutthichat,Andersson, Pher G.
supporting information
p. 13878 - 13883
(2018/10/24)

Copper-catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates: Synthesis of aryl/heteroaryl α-keto esters
A copper catalyzed Pummerer type reaction of α-thio aryl/heteroarylacetates is described for the first time. This transformation represents a new route to synthesize α-keto esters, which are important intermediates for pharmaceuticals and organic synthesis. The reaction proceeds via in situ generation of a thionium ion that undergoes hydrolysis to furnish α-keto esters in synthetically viable yields (up to 82%).
Saha, Pipas,Ray, Sumit Kumar,Singh, Vinod K.
p. 1765 - 1769
(2017/04/13)

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
supporting information
p. 2869 - 2872
(2017/06/13)

METHODS FOR USING TRIAZOLO-PYRAZINYL SOLUBLE GUANYLATE CYCLASE ACTIVATORS IN FIBROTIC DISORDERS
Provided are methods for treating or preventing a fibrotic disease selected from systemic sclerosis, cystic fibrosis, non-alcoholic steatohepatitis, Peyronie's disease, or interstitial lung disease; the method comprising administering a therapeutically ef
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Page/Page column 87; 88

(2017/12/15)

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.
Usui, Yoshihiro,Uehara, Fumiaki,Hiki, Shinsuke,Watanabe, Kazutoshi,Tanaka, Hiroshi,Shouda, Aya,Yokoshima, Satoshi,Aritomo, Keiichi,Adachi, Takashi,Fukunaga, Kenji,Sunada, Shinji,Nabeno, Mika,Saito, Ken-Ichi,Eguchi, Jun-ichi,Yamagami, Keiji,Asano, Shouichi,Tanaka, Shinji,Yuki, Satoshi,Yoshii, Narihiko,Fujimura, Masatake,Horikawa, Takashi
p. 3726 - 3732
(2017/07/27)

α-Alkoxycarbonyl-α-hydroxy secondary amides from a carbamoylsilane and α-ketoesters
The addition of N-methoxymethyl-N-organylcarbamoyl(trimethyl)silane to α-ketoesters in anhydrous toluene at 60 °C afforded α-alkoxycarbonyl-α-siloxy amides in high yields (75–96%). The methoxymethyl was used as an amino protecting group and could be easily converted into hydrogen atom by simple acid hydrolysis leading to α-alkoxycarbonyl-α- hydroxy secondary amides.
Li, Weidong,Han, Yuling,Chen, Jianxin
p. 5813 - 5819
(2017/09/05)

Br?nsted base-catalyzed three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement
A three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite under Br?nsted base catalysis was developed by utilizing the [1,2]-phospha-Brook rearrangement. The reaction involves the generation of ester enolates via the umpolung proc
Kondoh, Azusa,Terada, Masahiro
supporting information
p. 4704 - 4711
(2016/06/09)

IMIDAZO-PYRAZINYL DERIVATIVES USEFUL AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS
A compound of Formula I or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate ("cGMP") and are generally suitable for the therapy and prophylaxis of diseases which are associated w
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Page/Page column 36

(2016/12/22)

IMIDAZO-PYRAZINYL DERIVATIVES USEFUL AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS
A compound of Formula I or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate ("cGMP") and are generally suitable for the therapy and prophylaxis of diseases which are associated w
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Page/Page column 42

(2016/12/16)

PYRAZOLINE-3-ON DERIVATIVE AND HERBICIDE CONTAINING THE SAME AS ACTIVE INGREDIENT
PROBLEM TO BE SOLVED: To provide a compound having excellent weed controlling effect and useful as an active ingredient of a herbicide. SOLUTION: There are provided a pyrazoline-3-on derivative represented by the following formula (1), where R1
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Paragraph 0176

(2016/10/08)

PYRAZOLINE-3-ON DERIVATIVE, MANUFACTURING METHOD THEREFOR AND HERBICIDE CONTAINING THE SAME AS ACTIVE INGREDIENT
PROBLEM TO BE SOLVED: To provide a compound having excellent weed controlling effect and useful as an active ingredient of a herbicide. SOLUTION: There are provided a herbicide containing a pyrazoline-3-on derivative represented by the following formula (
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Paragraph 0098

(2016/10/09)

A novel method for synthesis of α-keto esters with phenyliodine(III) diacetate
A rapid and efficient synthesis of α-keto esters from β-ketonitriles using phenyliodine(III) diacetate is reported. This protocol gave α-keto esters in good yields. This is the first time to report the application of hypervalent iodine(III) reagents in the synthesis of α-keto esters. A plausible reaction mechanism is proposed.
Xie, Yuanyuan,Liu, Jiwei,Huang, Yingyi,Yao, Lixia
supporting information
p. 3793 - 3795
(2015/06/08)

Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates
Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.
Feng, Chao,Feng, Daming,Loh, Teck-Peng
supporting information
p. 342 - 345
(2015/01/09)

PRODRUGS OF HIV REVERSE TRANSCRIPTASE INHIBITORS
Compounds of Formula I are described: wherein R1 and R2 are defined herein. The compounds of Formula I are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV, and the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
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Page/Page column 38; 39

(2015/12/30)

IMIDAZO-PYRAZINE DERIVATIVES USEFUL AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS
A compound of Formula II or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate ("cGMP") and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of Formula II, or a pharmaceutically acceptable salt thereof, for their use in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of Formula II or a pharmaceutically acceptable salt thereof.
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(2016/04/04)

2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction
Highly efficient catalyst free methods for the synthesis of α-hydroxy-β-oxophosphonates and α-oxoesters have been described. The existence of a 2-oxo group in α-oxoaldehydes is a key factor in promoting the reaction of the tervalent phosphite form towards 2-oxoaldehydes in the synthesis of α-hydroxy-β-oxophosphonates. The in situ activated α-C-H atom of α-hydroxy-β-oxophosphonates sustains aerobic intramolecular nucleophilic displacement in a curious way to produce α-oxoester.
Battula, Satyanarayana,Battini, Narsaiah,Singh, Deepika,Ahmed, Qazi Naveed
supporting information
p. 8637 - 8641
(2015/08/24)

NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
Compounds of Formula I: are HIV reverse transcriptase inhibitors, wherein R1, R2, RE, L, M and Z are defined herein. The compounds of Formula I and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines
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(2014/04/18)

5-PHENOXY-3H-PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS HIV REVERSE TRANSCRIPTASE INHIBITORS
Compounds of Formula (I) are HIV reverse transcriptase inhibitors, wherein R1, R2, RE, L, M and Z are defined herein. The compounds of Formula (I) and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
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Page/Page column 114

(2014/05/07)

Rhodium(III)-catalyzed olefinic C-H alkynylation of acrylamides using tosyl-imide as directing group
The Rh(III)-catalyzed C-H alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.
Feng, Chao,Feng, Daming,Luo, Yang,Loh, Teck-Peng
supporting information
p. 5956 - 5959
(2015/01/08)

Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides
Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98 % ee). This is realized by the use of the cationic iridium complex [Ir(cod) 2](BArF4) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM. Carbon's got a brand new bond: Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities. This is realized by the use of an asymmetric cationic iridium complex formed in situ (see Scheme).
Shirai, Tomohiko,Ito, Hajime,Yamamoto, Yasunori
supporting information
p. 2658 - 2661
(2014/03/21)

PIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CANCER
The present invention relates to piperazinyl derivatives of formula (I) and the use thereof as a drug, particularly for the treatment of cancer, the pharmaceutical compositions containing said derivatives, and the method for synthesising same.
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Paragraph 0110-0112

(2014/12/09)

Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes
Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis-trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β-CF3-functionalized acrylamide derivatives. Copyright
Feng, Chao,Loh, Teck-Peng
supporting information
p. 122414 - 122417
(2013/12/04)

Electrochemical synthesis of the aryl α-ketoesters from acetophenones mediated by Ki
Two C-O bonds formed in one step: The oxidative coupling reaction of acetophenones with alcohol was developed by a dioxygen activation to afford α-ketoesters under electrochemical conditions. This novel transformation not only provides a simple and efficient approach to synthetize α-ketoester derivatives, but also invents a new strategy to construct a C-O bond by virtue of an anode oxidation (see scheme). Copyright
Zhang, Zhenlei,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
supporting information
p. 17711 - 17714
(2014/01/17)

Peptide-catalyzed stereoselective conjugate addition reactions generating all-carbon quaternary stereogenic Centers
A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β-disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ-Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products. Copyright
Kastl, Robert,Wennemers, Helma
supporting information
p. 7228 - 7232
(2013/07/26)

Direct asymmetric aldol addition-isomerization of α,β- unsaturated γ-butyrolactam with aryl α-ketoesters: Synthesis of MBH-type products
A highly efficient direct asymmetric aldol addition-isomerization reaction at the α-position of α,β-unsaturated γ-butyrolactam and aryl α-ketoesters by using a bifunctional thiourea catalyst was achieved. Morita-Baylis-Hillman type adducts containing a quaternary stereocenter can be obtained in high yields and with excellent enantioselectivities (up to 99% ee). The Royal Society of Chemistry 2013.
Zhang, Jinlong,Liu, Xihong,Ma, Xiaojuan,Wang, Rui
supporting information
p. 3300 - 3302
(2013/06/04)

Azastilbenes: A cut-off to p38 MAPK inhibitors
Inhibitors with vicinal 4-fluorophenyl/4-pyridine rings on a five- or six-membered heterocyclic ring are known to inhibit the p38 mitogen-activated protein kinase (MAPK), which is a potential target for rheumatoid arthritis and several different types of cancer. Several substituted azastilbene-based compounds with vicinal 4-fluorophenyl/4-pyridine rings were designed using computational docking, synthesized, and evaluated in a cell-free radiometric p38α assay. The biochemical evaluation shows that the best inhibition (down to 110 nM) is achieved for azastilbene-based compounds having an isopropylamine substituent in the 2-position of the pyridine ring. The inhibition of p38 signaling in human breast cancer cells was observed for two of the compounds. The Royal Society of Chemistry 2013.
Poon, Jia-Fei,Alao, John Patrick,Sunnerhagen, Per,Dinér, Peter
p. 4526 - 4536
(2013/08/23)

PYRROLIDINE-FUSED THIADIAZINE DIOXIDE COMPOUNDS AS BACE 1NHIBITORS, COMPOSITIONS, AND THEIR USE
In its many embodiments, the present invention provides provides certain iminothiadiazine dioxide compounds, including compounds Formula (I): and tautomers and stereoisomers thereof, and pharmaceutically acceptable salts of said compounds, said tautomeros and said stereoisomers, where in each of W, Z, R1H, R2, R3, R4, ring A, ring B, m, n, p, and- L1 - is as defined herein. The novel compounds of the invention have surprisingly been found to exhibit properties which are expected to render them advantageous as BACE inhibitors and/or for the treatment and prevention of various pathologies related there to. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use, including Alzheimer?s disease, are also disclosed
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(2012/10/18)

Catalytic enantioselective protonation of α-oxygenated ester enolates prepared through phospha-brook rearrangement
(Chemical Equation Presented) Phosphonates go chiral: The organocatalytic enantioselective reaction of α-ketoesters with phosphites using cinchona alkaloids and Na2CO3 has afforded α-phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol% does not result in a significant decrease of the enantioselectivity.
Hayashi, Masashi,Nakamura, Shuichi
supporting information; experimental part
p. 2249 - 2252
(2011/04/16)

Enantioselective enolate protonation in sulfamichael addition to r-substituted n-acryloyloxazolidin-2-ones with bifunctional organocatalyst
Organocatalytic conjugate addition of thiols to R-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules. 2011 American Chemical Society.
Rana, Nirmal K.,Singh, Vinod K.
supporting information; experimental part
p. 6520 - 6523
(2012/02/01)

BF3 · Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates in acetonitrile: A novel approach to 2,3-diaryl β-enamino ester derivatives
The BF3·Et2O-induced decomposition of ethyl 2-diazo-3-hydroxy-3,3-diarylpropanoates, prepared by the addition of a series of benzophenones to ethyl diazo(lithio)acetate, is reported and studied. By using acetonitrile as a solvent, the corresponding N-acyl β-enamino ester derivatives are obtained in good yields and with a diverse regioselectivity as the result of 1,2-aryl migration in the vinyl cation intermediates. The factors that govern the migratory aptitude as well as the mechanistic aspects of the reaction are discussed.
Gioiello, Antimo,Venturoni, Francesco,Natalini, Benedetto,Pellicciari, Roberto
supporting information; experimental part
p. 3520 - 3523
(2009/09/30)

N-SUBSTITUTED GLYCINE DERIVATIVES: HYDROXYLASE INHIBITORS
The invention described herein relates to certain pyridazinedione N-substituted glycine derivatives of formula (I) which are antagonists of HIF prolyl hydroxylases and are useful for treating diseases benefiting from the inhibition of this enzyme, anemia being one example
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Page/Page column 34

(2008/12/07)

CeCl3·7H2O: An effective additive in ru-catalyzed enantioselective hydrogenation of aromatic α-ketoesters
(Chemical Equation Presented) In the presence of catalytic amounts of CeCl3·7H2O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic α-ketoesters. A variety of ethyl α-hydroxy-α-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic α-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3·7H2O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3·7H2O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.
Meng, Qinghua,Sun, Yanhui,Ratovelomanana-Vidal, Virginie,Genet, Jean Pierre,Zhang, Zhaoguo
p. 3842 - 3847
(2008/09/21)

Synthesis of α-keto esters by the rhodium-catalysed reaction of cyanoformate with arylboronic acids
An arylrhodium(i) species selectively reacts with the cyano group of ethyl cyanoformate to afford the corresponding α-keto ester in good yield. The Royal Society of Chemistry.
Shimizu, Hiroshi,Murakami, Masahiro
p. 2855 - 2857
(2008/02/08)

Synthesis of aryl α-keto esters via the rearrangement of aryl cyanohydrin carbonate esters
A facile synthesis of aryl α-keto esters is reported involving the rearrangement of aryl cyanohydrin carbonate esters induced by the α-carbanion to the nitrile group generated by LDA. However, under similar conditions, an o-benzyloxycyanohydrin carbonate ester rearranged via a domino reaction leading to 2-phenylbenzofuran-3-carboxylic acid.
Thasana, Nopporn,Prachyawarakorn, Vilailak,Tontoolarug, Sopchok,Ruchirawat, Somsak
p. 1019 - 1021
(2007/10/03)

Photochemical reactions of alkyl phenylglyoxylates
Three new photoproducts, ethyl O-benzoyl mandelate (5a), ethyl O-acetylmandelate (6a), and biphenyl triketone (7a) are isolated and identified in the reactions of ethyl phenylglyoxylate (1a) in benzene. Quantum yields and initial rate constants of product formation are shown to be concentration dependent. For the formation of carbonyl product 3 at lower starting material concentrations (N) and intermolecular H abstraction (k1) of methyl phenylglyoxylate (1d) are measured.
Hu, Shengkui,Neckers, Douglas C.
p. 6407 - 6415
(2007/10/03)

Reaction of Organometallic Reagebts with Ethyl Trifluoroacetate and Diethyl Oxalate. Formation of Trifluoromethyl Ketones and α-Keto Esters via Stable Tetrahedral Adducts
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Creary, Xavier
p. 5026 - 5030
(2007/10/02)