cas 73790-09-7, ETHYL 2-(2-NAPHTHYL)-2-OXOACETATE

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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)

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling
A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.
Li, Bowen,Aliyu, Muinat A.,Gao, Zhenhua,Li, Tiejun,Dong, Wei,Li, Junchen,Shi, Enxue,Tang, Wenjun
supporting information
p. 4974 - 4978
(2020/07/03)

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)

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)

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 TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters
A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.
Zhou, Peng-Jun,Li, Cheng-Kun,Zhou, Shao-Fang,Shoberu, Adedamola,Zou, Jian-Ping
p. 2629 - 2637
(2017/04/03)

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters
A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.
Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
p. 12247 - 12257
(2016/12/23)

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)

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 000853

(2015/04/15)

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)

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)

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)

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)

2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids
Nitroarylacetates are useful small molecular building blocks that act as precursors to α-ketoesters and aryl nitromethanes as well as α-amino acids. Methods were developed that produce each of these compound types in good yields. Two different conditions
Metz, Alison E.,Kozlowski, Marisa C.
p. 717 - 722
(2013/02/25)

Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3
A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.
Infante, Rebeca,Nieto, Javier,Andres, Celia
supporting information; experimental part
p. 4375 - 4379
(2012/05/20)

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)

Direct synthesis of α-keto esters from ethylbenzenes using 48% aqueous HBr by aerobic visible light photooxidation
We report that ethylbenzenes can be directly oxidized to the corresponding -keto esters with molecular oxygen in the presence of 48% aqueous HBr under visible light irradiation. This synthetic procedure is the first example for direct preparation of the corresponding α-keto esters from ethylbenzenes. Georg Thieme Verlag Stuttgart - New York.
Tada, Norihiro,Ban, Kazunori,Nobuta, Tomoya,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
experimental part
p. 1381 - 1384
(2011/07/31)

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)

Chiral N-heterocyclic carbene ligands for asymmetric catalytic oxindole synthesis
The Pd-catalysed asymmetric intramolecular α-arylation of amide enolates containing heteroatom substituents gives chiral 3-alkoxy or 3-aminooxindoles in high yield and with enantioselectivities up to 97% ee when a new chiral N-heterocyclic carbene ligand is used. The Royal Society of Chemistry.
Jia, Yi-Xia,Hillgren, J. Mikael,Watson, Emma L.,Marsden, Stephen P.,Kuendig, E. Peter
supporting information; scheme or table
p. 4040 - 4042
(2009/03/11)

&α,&α-Difluoroarylacetic Acids: Preparation from (Diethylamino)sulfur Trifluoride and &α-Oxoarylacetates
Several α,α-difluoroarylacetic acids have been prepared by reaction of DAST ((diethylamino)sulfur trifluoride) with esters of α-oxoarylacetic acids and then hydrolysis of the resulting difluoro ester.Examples include the α,α-difluoro derivates of the synthetic plant auxin, α-naphthylacetic acid, and the antiinflammatory drug, ibufenac.
Middleton, W. J.,Bingham, E. M.
p. 2883 - 2887
(2007/10/02)