- Total Synthesis of Benzofuran-Based Aspergillusene B via Halogenative Aromatization of Enones
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A novel "non-aromatic pool" synthetic strategy for the synthesis of benzofuran-based natural products via oxidative haloaromatization of enones is reported. This approach is successfully applied in the first total synthesis of the natural product aspergil
- Bhatti, Aisha,Grabovyi, Gennadii A.,Mohr, Justin T.
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- PROCESS FOR PREPARING CARBAMOYLOXYMETHYL TRIAZOLE CYCLOHEXYL ACID COMPOUNDS
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Improved methods and intermediates thereof for preparing carbamoyloxy methyl triazole cyclohexyl acid compounds are described. These compounds are useful as LPA antagonists. Formula (I).
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Page/Page column 81; 83-84
(2020/10/27)
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- Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones
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Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or 3-(alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.
- Do Van Thanh, Nhan,Patra, Subrata,Clive, Derrick L.J.
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p. 4343 - 4350
(2018/07/13)
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- Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis
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A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g
- Liao, Li-Li,Gui, Yong-Yuan,Zhang, Xiao-Bo,Shen, Guo,Liu, Hui-Dong,Zhou, Wen-Jun,Li, Jing,Yu, Da-Gang
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supporting information
p. 3735 - 3738
(2017/07/26)
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- Asymmetric Sequential Cu-Catalyzed 1,6/1,4-Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity
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The first stereocontrolled Cu-catalyzed sequential 1,6/1,4-asymmetric conjugate addition (ACA) of C-metalated hard nucleophiles to cyclic dienones is reported. The use of DiPPAM (diphenylphosphinoazomethinylate) followed by a phosphoramidite as the stereo
- Blons, Charlie,Morin, Marie S. T.,Schmid, Thibault E.,Vives, Thomas,Colombel-Rouen, Sophie,Baslé, Olivier,Reynaldo, Thibault,Covington, Cody L.,Halbert, Stéphanie,Cuskelly, Sean N.,Bernhardt, Paul V.,Williams, Craig M.,Crassous, Jeanne,Polavarapu, Prasad L.,Crévisy, Christophe,Gérard, Hélène,Mauduit, Marc
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supporting information
p. 7515 - 7525
(2017/06/06)
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- Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones
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A palladium-catalyzed decarboxylative coupling reaction was developed for the synthesis of 3-(1-alkynyl)-2-cyclohexen-1-ones. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to afford the corresponding enynones in good
- Yu, Subeen,Cho, Eunjeong,Kim, Jimin,Lee, Sunwoo
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p. 11150 - 11156
(2017/10/27)
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- An unusual pathway to cyclobutane formation via desulfurative intramolecular photocycloaddition of an enone benzothiazoline pair
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Irradiation of the enone benzothiazoline 3 leads to the formation of cyclobutane 5. Preliminary mechanistic studies establish the intermediacy of an enecarbamate 14 in this photochemical transformation, which could be the result of sulfur extrusion from an episulfide intermediate. Photocycloaddition of the enecarbamate intermediate 14 leads to the formation of "crossed" photoadducts, i.e., 5, in excellent yield, with high levels of regio- and stereochemical control.
- Jo, Hyunil,Fitzgerald, Mark E.,Winkler, Jeffrey D.
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supporting information; experimental part
p. 1685 - 1687
(2009/08/15)
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- First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction
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The palladium-catalyzed cross coupling Heck reaction of tosylate (2) and methyl acrylate has been developed as an efficient method for carbon-carbon bond formation. The tosylate (2) was reacted with methyl acrylate using palladium acetate as catalyst to p
- Fu, Xiaoyong,Zhang, Shuyi,Yin, Jianguo,McAllister, Timothy L.,Jiang, S.Anna,Tann, Chou-Hong,Thiruvengadam,Zhang, Fucheng
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p. 573 - 576
(2007/10/03)
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- A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes
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A copper-free palladium-catalyzed cross coupling of vinyl tosylate (2) and terminal acetylenes was investigated, affording a convenient and efficient method for construction of an sp-sp2 carbon-carbon bond. The tosylate (2) derived from 1,3-cyc
- Fu, Xiaoyong,Zhang, Shuyi,Yin, Jianguo,Schumacher, Doris P.
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p. 6673 - 6676
(2007/10/03)
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- Investigation of the N-substituent conformation governing potency and μ receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3- hydroxyphenyl)piperidine opioid antagonists
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A study of the binding site requirements associated with the N- substituent of (+)-(3R,4R)dimethyl-4-(3-hydroxyphenyl)piperidine (4) derivatives was undertaken using a set of rigid vs flexible N-substituents. The study showed that compounds 7-9 bearing th
- Thomas, James B.,Wayne Mascarella,Rothman, Richard B.,Partilla, John S.,Xu, Heng,McCullough, Karen B.,Dersch, Christina M.,Cantrell, Buddy E.,Zimmerman, Dennis M.,Carroll, F. Ivy
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p. 1980 - 1990
(2007/10/03)
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- Enantioselective allene/enone photocycloadditions: The use of an inexpensive optically active 1,3-disubstituted allene
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We report the preparation and use of an inexpensive readily prepared optically active 1,3-disubstituted allene that may be utilized for enantioselective intramolecular allene/enone photocycloadditions. In addition, we describe novel substrates for intramo
- Shepard, Mary S.,Carreira, Erick M.
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p. 16253 - 16276
(2007/10/03)
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- Facile Deoxygenation of Phenols and Enols Using Sodium Borohydride-Nickel Chloride
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A facile deoxygenation reaction of phenol and 1,3-dicarbonyl compounds was investigated.Phenols, enolizable 1,3-diketones and 3-ketoesters were converted into the toluene-p-sulfonates which were reduced by a sodium borohydride-nickel chloride system to give the deoxygenated aromatic compounds, alcohols and esters, respectively.
- Wang, Feng,Chiba, Kazuhiro,Tada, Masahiro
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p. 1897 - 1900
(2007/10/02)
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- Reversible Cyclization of N-(3-Hydroxy-1-Alkenyl)Pyridinium Salts to Pyridooxazines
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Partially hydrogenated pyridooxazine, cyclopentapyridooxazine and pyridobenzoxazine ring systems were easily formed in the reaction of 3-hydroxy-2-(2-hydroxy-1,3-dioxo-2-indanyl)-2-alken-1-one derivatives with tosyl chloride and pyridine bases.A facile interconversion between pyridooxazines and the corresponding pyridinium salts was also realized.
- Carotti, A.,Casini, G.,Ferappi, M.,Cingolani, G. M.
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p. 1577 - 1584
(2007/10/02)
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