105166-35-6Relevant academic research and scientific papers
Broad scope hydrofunctionalization of styrene derivatives using iron-catalyzed hydromagnesiation
Jones, Alison S.,Paliga, James F.,Greenhalgh, Mark D.,Quibell, Jacob M.,Steven, Alan,Thomas, Stephen P.
, p. 5964 - 5967 (2014)
The highly regioselective iron-catalyzed formal hydrofunctionalization of styrene derivatives with a diverse range of electrophiles has been developed using a single, operationally simple hydromagnesiation procedure and only commercially available, bench-stable reagents. Using just 0.5 mol % FeCl2·4H2O and N,N,N',N'-tetramethylethylenediamine, hydromagnesiation and electrophilic trapping have been used to form new carbon-carbon bonds (13 examples) and carbon-heteroatom bonds (5 examples) including the products of formal cross-coupling reactions, hydroboration, hydroamination, hydrosilylation, and hydrofluorination.
Ni-Catalyzed C(sp3)–O Arylation of α-Hydroxy Esters
Monteith, John J.,Rousseaux, Sophie A. L.
, p. 9485 - 9489 (2021/12/09)
A Negishi cross-coupling of α-hydroxy ester derivatives and arylzinc reagents has been developed. This reaction tolerates both primary and secondary C(sp3)–O alcohol precursors and achieves efficient cross-coupling under Ni catalysis without the need for added external metal reductant, photocatalyst, or additives. The arylation of readily accessible C(sp3)–O electrophiles in this operationally simple, rapid, and mild reaction provides a complementary way of accessing desirable α-aryl ester products.
Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases
Sandoval, Braddock A.,Meichan, Andrew J.,Hyster, Todd K.
supporting information, p. 11313 - 11316 (2017/08/30)
Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.
A versatile synthesis of O-desmethylangolensin analogues from methoxy-substituted benzoic acids
Hong, Hyo Jeong,Lee, Jae In
, p. 569 - 574 (2015/02/05)
The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using Pb(OAc)4/HClO4 in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di- 2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-α-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.
Pd-catalyzed decarboxylative cross-couplings of potassium malonate monoesters with aryl halides
Feng, Yi-Si,Wu, Wei,Xu, Zhong-Qiu,Li, Yan,Li, Ming,Xu, Hua-Jian
, p. 2113 - 2120 (2012/03/26)
An efficient catalytic protocol for Pd-catalyzed decarboxylative cross-coupling of potassium malonate monoesters and derivatives with aryl bromides and chlorides are described. Because of its broad applicability, this new catalytic system provides an alternative method for the preparation of diverse aryl acetic acids and derivatives.
BENZOAZEPIN-OXY-ACETIC ACID DERIVATIVES AS PPAR-DELTA AGONISTS USED FOR THE INCREASE OF HDL-C, LOWER LDL-C AND LOWER CHOLESTEROL
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Page/Page column 53-54, (2008/06/13)
The invention is directed to compounds of Formula (I) useful as PPAR agonists. Pharmaceutical compositions and methods of treating one or more conditions including, but not limited to, diabetes, nephropathy, neuropathy, retinopathy, polycystic ovary syndr
BICYCLIC DERIVATIVES AS PPAR MODULATORS
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Page/Page column 59, (2008/06/13)
The present invention is directed to compounds represented by the following structural formula, Formula (I), and stereoisomers, pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: (a) R2 is selected from the group consisting of C0-C8 alkyl and C1-4- heteroalkyl; (b) X is selected from the group consisting of a single bond, O, S, S(O)2 and N; (c) U is an aliphatic linker wherein one carbon atom of the aliphatic linker is optionally replaced with O, NH or S, and wherein such aliphatic linker is optionally substituted with from one to four substituents each independently selected from R30; (d) Y is selected from the group consisting of C, O, S, NH and a single bond; and (e) E is C(R3)(R4)A or A.
Bridged-ring Nitrogen Compounds. Part 7. Synthesis of the 1,4-Ethano-3-benzazepine Ring System
Sedgeworth, Janette,Proctor, George R.
, p. 2677 - 2688 (2007/10/02)
9-Bromobenzosuberone was converted via 9-cyanobenzosuberone into several other 9-substituted benzosuberones, but attemps to cause them to cyclise to the tricyclic 1,4-ethano-3-benzazepine ring system were unsuccessful.Both ethyl phenylacetate and ethyl 3-methoxyphenylacetate were converted by conventional procedures into the corresponding 6,7,8,9-tetrahydro-5-methyl-9,10-dioxo-5,8-methano-5H-benzocycloheptenes.The 3-methoxy derivative was further converted into N-benzyl-8-bromo-6,7,8,9-tertrahydro-3-methoxy-5-methyl-9-oxo-5H-benzocycloheptene-5-carboxamide which could be converted into the tricyclic 3-benzyl-2,3,4,5-tetrahydro-8-methoxy-1-methyl-2,5-dioxo-1,4-ethano-1H-3-benzazepine and thence in two steps into both 3-benzyl-2,3,4,5-tetrahydro-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepine and 3-benzyl-2,3,4,5-tetrahydro-8-hydroxy-1-methyl-1,4-ethano-1H-3-benzazepine.Also prepared were 3-benzyl-2,3,4,5-tetrahydro-5-hydroxy-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepine and 3-benzyl-3,4-dihydro-8-methoxy-1-methyl-1,4-ethano-1H-3-benzazepin-5(2H)-one.
