66790-58-7Relevant academic research and scientific papers
Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes
Stegbauer, Simone,Jandl, Christian,Bach, Thorsten
supporting information, p. 14593 - 14596 (2018/10/15)
Visible-light irradiation (λ=457 nm) enabled the enantioselective ortho photocycloaddition of olefins to phenanthrene-9-carboxaldehydes (15 examples, 46–93 % yield, 82–98 % ee). A chiral oxazaborolidine Lewis acid (20 mol %) was employed as the catalyst. It operates by coordination to the aldehyde inducing a bathochromic absorption shift beyond the nπ* absorption of the uncomplexed aldehyde. At long wavelengths the Lewis acid complex is exclusively excited; within the complex, one enantiotopic face of the aromatic aldehyde is efficiently shielded. Lewis acid coordination also alters the type selectivity and the simple diastereoselectivity of the photocycloaddition.
Site- and regio-selective incorporation of carbon dioxide into the C(sp2)Si bond of benzosilacyclobutenes
Ishida, Naoki,Okumura, Shintaro,Murakami, Masahiro
supporting information, p. 570 - 572 (2018/04/12)
A reaction of benzosilacyclobutenes with carbon dioxide is catalyzed by a nickel complex having an N-heterocyclic carbene ligand. Carbon dioxide inserts into the C(sp2)Si bond in a site- and regio-selective manner to form a carboncarbon bond, furnishing benzoic acid derivatives.
Intramolecular Direct Arylation of 1,3-Diketone-Derived Enol Ethers in a Synthesis of Tricyclic Oxoisochromene Derivatives
Muimhneacháin, Eoin ó,Pardo, Leticia M.,Bateman, Lorraine M.,Rao Khandavilli,Lawrence, Simon E.,McGlacken, Gerard P.
supporting information, p. 1529 - 1534 (2017/05/05)
A synthesis of tricyclic oxoisochromene derivatives via an intramolecular direct arylation of cycloalkyl-1,3-diketone-derived α,β-unsaturated ketone substrates is described. Interesting mechanistic insight has been gathered, based on deuterium migration s
Regioisomerism in the synthesis of a chiral aminotetralin drug compound: Unraveling mechanistic details and diastereomer-specific in-depth NMR investigations
Schuisky, Peter,Federsel, Hans-Juergen,Tian, Wei
experimental part, p. 5503 - 5514 (2012/09/07)
During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue origin
Palladium(0)-catalyzed arylative dearomatization of phenols
Rousseaux, Sophie,Garcia-Fortanet, Jorge,Del Aguila Sanchez, Miguel Angel,Buchwald, Stephen L.
supporting information; experimental part, p. 9282 - 9285 (2011/08/04)
The palladium-catalyzed arylative dearomatization of phenols to yield spirocyclohexadienone products in good to excellent yields has been developed. Preliminary results demonstrate that the formation of the spirocyclic all-carbon quaternary center can be accomplished with high levels of enantiocontrol (up to 91% ee).
BICYCLIC DERIVATIVES AS PPAR MODULATORS
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Page/Page column 76-77, (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.
Synthesis of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis
Harvey, Ronald G.,Dai, Qing,Ran, Chongzhao,Penning, Trevor M.
, p. 2024 - 2032 (2007/10/03)
Efficient new syntheses of the o-quinone derivatives of benzo[a]pyrene (BPQ), 7,12-dimethylbenz-[a] anthracene (DMBAQ), and benz[a]anthracene (BAQ), implicated as active carcinogenic metabolites of the parent polycyclic aromatic hydrocarbons (PAHs), are reported. These PAH quinones also serve as starting compounds for the synthesis of the other active metabolites of these PAHs thought to be involved in their mechanism(s) of carcinogenesis. The latter include the corresponding o-catechols, trans-dihydrodiols, and the corresponding anti- and syn-diol epoxides.
A new synthesis of 3-substituted-1H-indenes through reaction of o-(β-magnesioalkyl)phenylmagnesium dihalides with carboxylate esters
Baker, Robert W.,Foulkes, Michael A.,Griggs, Michael,Nguyen, Bao N.
, p. 9319 - 9322 (2007/10/03)
A new synthesis of 3-substituted-1H-indenes has been developed through the reaction of o-(β-magnesioalkyl)phenylmagnesium dihalides with carboxylate esters, followed by dehydration of the intermediate 1-substituted-1-indanols. Di-Grignard reagents allowing the synthesis of 3-substituted-, 2-methyl-3-substituted-, and 4-methyl-3-substituted-1H-indenes have been prepared, with overall yields for the two-step sequence ranging from 45 to 95%.
Method for preparing substituted benzyl bromides
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, (2008/06/13)
PCT No. PCT/EP98/04485 Sec. 371 Date Jan. 11, 2000 Sec. 102(e) Date Jan. 11, 2000 PCT Filed Jul. 20, 1998 PCT Pub. No. WO99/06339 PCT Pub. Date Feb. 11, 1999Substituted benzyl bromides of the formula I where at least one substituent R1-5 is an electron-at
Selective Oxidation of 2-Bromo-m-xylene to 2-Bromo-3-methylbenzoic Acid or 2-Bromoisophthalic Acid
Miyano, Sotaro,Fukushima, Hiroshi,Inagawa, Hideho,Hashimoto, Harukichi
, p. 3285 - 3286 (2007/10/02)
Aqueous sodium dichromate oxidation of 2-bromo-m-xylene (1) under a carbon dioxide pressure gave 2-bromoisophthalic acid (58percent), while NBS-bromination of 1 followed by Sommelet oxidation to aldehyde and then potassium permanganate oxidation enabled t
