- Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway
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The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.
- Hazra, Chinmoy Kumar,Jeong, Jinhoon,Kim, Hyunjoong,Baik, Mu-Hyun,Park, Sehoon,Chang, Sukbok
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supporting information
p. 2692 - 2696
(2018/02/09)
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- Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis
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An intermolecular condensation of alkynols and terminal alkynes is reported. Using IPrAuNTf2, an efficient Au-catalyzed cyclization-alkynylation strategy furnishes (2-arylalkynyl) cyclic ethers in moderate to excellent yields (up to 94%). This strategy is extended to the synthesis of functionalized 2,3-dihydrooxepines via the sequential Au-catalyzed ring expansion of the cyclic ether substrates.
- Smith, Courtney A.,Motika, Stephen E.,Wojtas, Lukasz,Shi, Xiaodong
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supporting information
p. 2315 - 2318
(2017/02/23)
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- Targeting an Aromatic Hotspot in Plasmodium falciparum 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase with β-Arylpropyl Analogues of Fosmidomycin
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Blocking the 2-C-methyl-d-erythrithol-4-phosphate pathway for isoprenoid biosynthesis offers new ways to inhibit the growth of Plasmodium spp. Fosmidomycin [(3-(N-hydroxyformamido)propyl)phosphonic acid, 1] and its acetyl homologue FR-900098 [(3-(N-hydroxyacetamido)propyl)phosphonic acid, 2] potently inhibit 1-deoxy-d-xylulose-5-phosphate reductoisomerase (Dxr), a key enzyme in this biosynthetic pathway. Arylpropyl substituents were introduced at the β-position of the hydroxamate analogue of 2 to study changes in lipophilicity, as well as electronic and steric properties. The potency of several new compounds on the P. falciparum enzyme approaches that of 1 and 2. Activities against the enzyme and parasite correlate well, supporting the mode of action. Seven X-ray structures show that all of the new arylpropyl substituents displace a key tryptophan residue of the active-site flap, which had made favorable interactions with 1 and 2. Plasticity of the flap allows substituents to be accommodated in many ways; in most cases, the flap is largely disordered. Compounds can be separated into two classes based on whether the substituent on the aromatic ring is at the meta or para position. Generally, meta-substituted compounds are better inhibitors, and in both classes, smaller size is linked to better potency.
- Sooriyaarachchi, Sanjeewani,Chofor, René,Risseeuw, Martijn D. P.,Bergfors, Terese,Pouyez, Jenny,Dowd, Cynthia S.,Maes, Louis,Wouters, Johan,Jones, T. Alwyn,Van Calenbergh, Serge,Mowbray, Sherry L.
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p. 2024 - 2036
(2016/10/22)
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- Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis
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The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.
- Motika, Stephen E.,Wang, Qiaoyi,Akhmedov, Novruz G.,Wojtas, Lukasz,Shi, Xiaodong
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supporting information
p. 11582 - 11586
(2016/10/24)
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- The combination of relay and cooperative catalysis with a gold/palladium/brnsted acid ternary system for the cascade hydroamination/ allylic alkylation reaction
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The combination of relay and cooperative catalysis with a gold/palladium/Brnsted acid ternary system renders a cascade hydroamination/allylic alkylation reaction to provide an unprecedented entry to pyrrolidine derivatives in high yields. Copyright
- Wu, Hua,He, Yu-Ping,Gong, Liu-Zhu
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supporting information; experimental part
p. 975 - 980
(2012/05/20)
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- Phenyl derivatives comprising an acetylene group
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This invention is concerned with compounds of the formula I: wherein one of R5, R6 and R7 is and X1, X2, R1 to R12, m, n and o are as defined in the description, and pharmaceutically acceptable salts and/or esters thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.
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Page/Page column 22
(2010/02/15)
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- Coupling reactions of aryl bromides with 1-alkynols catalysed by a tetraphosphine/palladium catalyst
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cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 system catalyses efficiently the coupling reactions of aryl halides with a variety of alkynols such as propargyl alcohol, but-1-yn-4-ol, pent
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
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p. 1603 - 1606
(2007/10/03)
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