- Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones
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An effective asymmetric α-phenylation of methyl ketones with triphenylaluminium in the presence of (+)-benzopyranoisoxazolidine has been developed. The reaction proceeds via the in situ formation of a chiral N-alkoxyenamine and the subsequent diastereoselective nucleophilic phenylation to provide α-phenylated products in moderate to good yields, with high enantioselectivities.
- Takeda, Norihiko,Furuishi, Mizuki,Nishijima, Yuri,Futaki, Erika,Ueda, Masafumi,Shinada, Tetsuro,Miyata, Okiko
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supporting information
p. 8940 - 8943
(2018/12/10)
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- Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins
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Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.
- Méndez-Sánchez, Daniel,Mangas-Sánchez, Juan,Busto, Eduardo,Gotor, Vicente,Gotor-Fernández, Vicente
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p. 122 - 131
(2016/01/25)
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- Discovery of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1- methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity
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The discovery of novel acyclic amide cannabinoid-1 receptor inverse agonists is described. They are potent, selective, orally bioavailable, and active in rodent models of food intake and body weight reduction. A major focus of the optimization process was to increase in vivo efficacy and to reduce the potential for formation of reactive metabolites. These efforts led to the identification of compound 48 for development as a clinical candidate for the treatment of obesity.
- Lin, Linus S.,Lanza Jr., Thomas J.,Jewell, James P.,Liu, Fing,Shah, Shrenik K.,Qi, Hongbo,Tong, Xinchun,Wang, Junying,Xu, Suoyu S.,Fong, Tung M.,Shen, Chun-Pyn,Lao, Julie,Xiao, Jing Chen,Shearman, Lauren P.,Stribling, D. Sloan,Rosko, Kimberly,Strack, Alison,Marsh, Donald J.,Feng, Yue,Kumar, Sanjeev,Samuel, Koppara,Yin, Wenji,Van Der Ploeg, Lex H. T.,Goulet, Mark T.,Hagmann, William K.
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p. 7584 - 7587
(2007/10/03)
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- Reduction of diaryl alkenes by hypophosphorous acid-iodine in acetic acid
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A mixture of 50% aqueous H3PO2 and I2 (in catalytic amount) in HOAc efficiently reduces aryl alkenes to the corresponding alkanes in high yield. Addition of acetic anhydride to the medium results in ring-acetylation (or N-acetylation in the case of amines). H3PO2 costs only one-fifth as much as hydriodic acid on a mole basis and one mole of H3PO2 produces four moles of HI, resulting in a 20-fold cost advantage for H3PO2/I2 over aqueous HI as a source of HI.
- Fry, Albert J.,Allukian, Myron,Williams, Allison D.
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p. 4411 - 4415
(2007/10/03)
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- Regioselective Mg-promoted C-acylation of stilbene and acenaphthylene derivatives
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Treatment of stilbene and acenaphthylene derivatives with Mg turnings in the presence of aliphatic acid anhydrides and trimethylsilyl chloride (TMSCl) in N,N-dimethylformamide (DMF) brought about a facile and efficient cross-coupling to give C-acylation p
- Nishiguchi, Ikuzo,Yamamoto, Yoshimasa,Sakai, Masahiro,Ohno, Toshinobu,Ishino, Yoshio,Maekawa, Hirofumi
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p. 759 - 762
(2007/10/03)
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- On the π-π interaction in the benzylation of ketones
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The benzylation of a set of nine ketones provides enough information to establish how the ketone structure affects the existence of a π-π interaction. The presence of a phenyl moiety starting from the a-carbon atom and flexibility in cyclic ketones are st
- Diez-Barra, Enrique,Merino, Sonia,Sanchez-Verdu, Prado,Torres, Jose
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p. 11437 - 11448
(2007/10/03)
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- Solid-Liquid Phase-Transfer Catalysis without Solvent: Selective Mono- and Di-alkylation of Benzyl Methyl Ketone
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The alkylation of benzyl methyl ketone 1 has been performed by phase-transfer catalysis without solvent.Excellent yields of mono- 2 and di-alkyl derivatives 3 and 4 were obtained through general, selective and mild conditions.
- Aranda, Alfonso,Diaz, Angel,Diez-Barra, Enrique,Hoz, Antonio de la,Moreno, Andres,Sanchez-Verdu, Prado
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p. 2427 - 2430
(2007/10/02)
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- POTENTIAL ANTIDEPRESSANTS: 3-METHYL-6-DIMETHYLAMINO-1,2-DIPHENYLHEXAN-3-OL AND RELATED COMPOUNDS
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3,4-Diphenylbutan-2-one (III) and 3-methyl-3-phenylbutan-2-one were transformed by treatment with 3-dimethylaminopropylmagnesium chloride and 1-methyl-4-piperidylmagnesium chloride to the amino alcohols VI, VII, and X.Compound VI was dehydrated to the ole
- Cervena, Irena,Holubek, Jiri,Svatek, Emil,Valchar, Martin,Protiva, Miroslav
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p. 2564 - 2571
(2007/10/02)
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- ALKYLATION DIRECTE DE CETONES ET D'ALDEHYDES EN PRESENCE DE POTASSE SOLIDE EN SUSPENSION
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Dehydrated solid KOH, suspended in aprotic solvents, is used as a base for ketone and aldehyde alkylation.The best solvent as regards yields and selectivity is DME.The quantity of KOH depends on the carbonyl compound acidity.This method gives as good results as less convenient homogeneous conditions.
- Artaud, I.,Torossian, G.,Viout, P.
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p. 5031 - 5038
(2007/10/02)
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- Formation and Reactions of 1-Phenyl-2-propanone Dianion and Related Systems with Electrophilic Reagents
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1-Phenyl-2-propanone, 1,1-diphenyl-2-propanone, and 1-(4-methoxyphenyl)-2-propanone were converted to their dicarbanions 3, 4, and 31, respectively, and their reactions with a number of electrophilic reagents were examined.All three dianions gave a mixture of C-1 and C-3 alkylation products when treated with alkyl halides of higher reactivity, while only C-1 alkylations occurred when alkyl halides of lower reactivity were used.It was also found that the 1,1-diphenyl-2-propanone and the 1-(4-methoxyphenyl)-2-propanone dianions 4 and 31 gave a higher ratio of C-1/C-3 alkylation products than the 1-phenyl-2-propanone dianion 3.When dianion 3 was reacted with p-anisaldehyde and a number of protonating agents, electrophilic attack occurred exclusively at the C-3 position.The trends observed are analyzed, and mechanisms are proposed to account for the results obtained.
- Trimitsis, G. B.,Hinkley, J. M.,TenBrink, R.,Faburada, A. L.,Anderson, R.,et al.
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p. 2957 - 2962
(2007/10/02)
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- Aryl-oxo-heptenoic acids
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Novel 4-phenyl-4-substituted-5-oxo-7-aryl-heptanoic acids are prefaced by either of two synthetic processes. The first method involves the reaction of a 4-phenyl-4-substituted-5-oxo-hexanoic acid with an arylcarboxyaldehyde. The second method involves reaction of an arylcarboxaldehyde with an appropriate ketone, treatment of the product with an acrylic acid ester, followed by hydrolysis of the resulting ester. The compounds of the invention are prostaglandin antagonists and are particularly useful as topical anti-inflammatory agents.
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