- Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates
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An enantioconvergent synthesis of chiral cyclic allylboronates from racemic allylic bromides was achieved by using a guanidine–copper catalyst. The allylboronates were obtained with high γ/α regioselectivities (up to 99:1) and enantioselectivities (up to 99 % ee), and could be further transformed into diverse functionalized allylic compounds without erosion of optical purity. Experimental and DFT mechanistic studies support an SN2′ borylation process catalyzed by a monodentate guanidine–copper(I) complex that proceeds through a special direct enantioconvergent transformation mechanism.
- Ge, Yicen,Cui, Xi-Yang,Tan, Siu Min,Jiang, Huan,Ren, Jingyun,Lee, Nicholas,Lee, Richmond,Tan, Choon-Hong
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supporting information
p. 2382 - 2386
(2019/02/01)
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- Inhibitors of influenza viruses replication
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Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A compound is represented by Structural Formula (IA) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
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Page/Page column 381; 382
(2016/06/14)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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PROBLEM TO BE SOLVED: To provide inhibitors of influenza virus replication. SOLUTION: Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient comprise administering to the biological sample or patient an effective amount of a compound represented by structural formula (I) or a pharmaceutically acceptable salt thereof, where the values of structural formula (IA) are as described herein. A compound is represented by structural formula (IA) or a pharmaceutically acceptable salt thereof, where the values of structural formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0982
(2016/10/08)
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- Simple and efficient 1,3-isomerization of allylic alcohols using a supported monomeric vanadium-oxide catalyst
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Promotion by group high five: Silica-supported monomeric vanadium-oxide promoted the isomerization of various allylic alcohols, including under scaled-up and solvent-free reaction conditions. This catalyst also exhibited high reusability with no drop in activity.
- Mitsudome, Takato,Sueoka, Shoichiro,Ikeda, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 2879 - 2882
(2013/10/21)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A compound is represented by Structural Formula (IA) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (IA) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
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- Kinetic resolution of chiral cyclohex-2-enones by rhodium(I)/binap- catalyzed 1,2- and 1,4-additions
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The feasibility of kinetic resolutions of racemic monosubstituted cyclohex-2-enones by Rh/binap-catalyzed reactions was investigated. 1,2-Addition of AlMe3 to the 5-substituted derivatives furnished allylic alcohols in the matched case, while t
- Kolb, Andreas,Hirner, Sebastian,Harms, Klaus,Zezschwitz, Paultheo Von
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supporting information; experimental part
p. 1978 - 1981
(2012/06/18)
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- Rhodium-catalyzed enantioselective 1,2-addition of aluminum organyl compounds to cyclic enones
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(Chemical Equation Presented) A question of the ligand: The chemoselectivity of the rhodium-catalyzed addition of AlMe3 to cyclohex-2-enone is guided by the type of ligand used. Whereas use of an achiral {Rh(cyclooctadiene)} complex leads to a 1,4-addition, use of a {Rh(binap)} species gives highly enantioselective 1,2-additions. This unprecedented reaction can be used for stereoselective 1,2-methylations and arylations of cyclic enones (see scheme).
- Siewert, Juergen,Sandmann, Rene,Von Zezschwitz, Paultheo
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p. 7122 - 7124
(2008/09/17)
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- Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols
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(Matrix Presented) The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the Li-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both
- Gayet, Arnaud,Bertilsson, Sophie,Andersson, Pher G.
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p. 3777 - 3779
(2007/10/03)
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- Allylic alcohols via catalytic asymmetric epoxide rearrangement
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Epoxides using chiral lithium amides, but other than for a small subset of meso-epoxides, insufficient reactivity and enantioselectivity hamper the existing methods. Furthermore, the chiral reagents are often required in large excess. This study presents a general and highly enantioselective process that, in addition, is based on catalytic amounts (5 mol %) of enantiopure (1S,3R,4R)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane and lithium diisopropylamide as the stoichiometric base. The influence of structural modification of the catalyst is studied in terms of activity, enantioselectivity, and aggregation behavior. The utility of the process is demonstrated by its application to a variety of epoxide derivatives (≥94% ee for 11 out of 14 examples), including the formal syntheses of, e.g., a prostaglandin core unit, epibatidine, carbovir, faranal, and lasiol. The system is readily extended to the resolution of racemic epoxides, which allows access to highly enantioenriched epoxides or allylic alcohols, even at conversions near 50%.
- Soedergren, Mikael J.,Bertilsson, Sophie K.,Andersson, Pher G.
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p. 6610 - 6618
(2007/10/03)
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- A concise asymmetric synthesis of the pheromone 1-methylcyclohex-2-enol via a 'merged substitution-elimination reaction'
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The title compound is prepared (> 94% ee) by a three step synthesis from 1-methylcyclohexene via a 'merged substitution-elimination reaction' involving a phenylselenide ion.
- Hamon, David P. G.,Tuck, Kellie L.
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p. 941 - 942
(2007/10/03)
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- Asymmetric synthesis of cyclohex-2-enols: The examples of seudenol and analogues
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An efficient synthesis of enantiomerically pure cyclohex-2-enols from the reaction of 2-p-tolylsulfinyl cyclohexanols with (CF3CO)2O/Py and subsequent hydrogenolysis of the C-S bond with Li/Naphthalene, is reported. This strategy has been applied to the asymmetric synthesis of seudenol and 1-methylcyclohex-2-en-1-ol. New data on the rearrangement of the trifluoroacetate group when 2-p-tolylsulfinyl 1-methylcyclohexenols are treated under the Pummerer reaction conditions are also reported.
- Bueno,Carmen Carreno,Garcia Ruano,Hamdouchi
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p. 1237 - 1240
(2007/10/02)
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- A convenient synthesis of both enantiomers of seudenol and their conversion to 1-methyl-2-cyclohexen-1-ol (MCOL)
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PPL catalyzed transesterification of seudenol (2) in dry Et2O yielded both optically enriched enantiomers (≥95% ee). Epoxidation, mesylation and reductive ring opening furnished optically enriched MCOL (1).
- Johnston,Morgan,Oehlschlager,Ramaswamy
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p. 377 - 380
(2007/10/02)
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- SYNTHESIS OF (R)-1-METHYL-2-CYCLOHEXEN-1-OL, A CONSTITUENT OF THE AGGREGATION PHEROMONES OF DENDROCTONUS PSEUDOTSUGAE
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An efficient route for the synthesis of (R)-(+)-1-methyl-2-cyclohexen-1-ol from 1-cyclohexenemethanol using the Sharpless epoxidation method as the source of chirality is described.
- Hamon, David P. G.,Massy-Westropp, Ralph A.,Newton, Josephine L.
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p. 771 - 774
(2007/10/02)
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- Pheromone Synthesis, CXI. - An Enzyme-Mediated Synthesis of Both Enantiomers of Seudenol and 1-Methyl-2-cyclohexen-1-ol, the Aggregation Pheromones of Dendroctonus pseudotsugae
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Enzymatic resolution of seudenol acetate by pig liver esterase has led to an efficient preparation of both the enantiomers of seudenol and 1-methyl-2-cyclohexen-1-ol, the aggregation pheromones of the Douglas-fir beetle Dendroctonus pseudotsugae Hopkins.
- Mori, Kenji,Ogoche, Jondiko I.J.
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p. 903 - 906
(2007/10/02)
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- SYNTHESIS AND BIOACTIVITY OF OPTICALLY ACTIVE FORMS OF 1-METHYL-2-CYCLOHEXEN-1-OL, AN AGGREGATION PHERONOME OF DENDROCTONUS PSEUDOTSUAGE
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Both the enantiomers of 1-methyl-2-cyclohexen-ol, an aggregation pheromone of the female Douglas-fer beetle, were synthesized from the enantiomers of seudenol (3-methyl-2-cyclohexen-1-ol).The enantiomers were less active than the racemate of 1-methyl-2-cy
- Mori, K.,Hazra, B. G.,Pfeiffer, R. J.,Gupta, A. K.,Lindgren, B. S.
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p. 2249 - 2254
(2007/10/02)
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