- Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines
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A series of bifunctional phosphine oxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asymmetric hydrosilylation of ketimines. bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide displayed the highest enantioselectivity of 60%.
- Warner, Christopher J.A.,Berry, Sian S.,Jones, Simon
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- Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers
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We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl d-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.
- Zanato, Chiara,Pelagalli, Alessia,Marwick, Katie F. M.,Piras, Monica,Dall'Angelo, Sergio,Spinaci, Andrea,Pertwee, Roger G.,Wyllie, David J. A.,Hardingham, Giles E.,Zanda, Matteo
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p. 2086 - 2096
(2017/03/11)
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- Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
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The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
- Mikhaylov, Andrey A.,Dilman, Alexander D.,Novikov, Roman A.,Khoroshutina, Yulia A.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.
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supporting information
p. 11 - 14
(2015/12/23)
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- Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans
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The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.
- Wang, Yanan,Jiang, Min,Liu, Jin-Tao
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supporting information
p. 1322 - 1327
(2016/04/26)
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- Cycloalkane aldehydes, method for preparing same, and use thereof in the perfume industry
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The invention relates to a compound of general formula I represented below: wherein: R1, R2 and R3 each independently represent a hydrogen atom or saturated or unsaturated, branched or non-branched C1 to C5 alkyl group;m is an integer between 1 and 4;n is an integer between 2 and 4; characterized in that the ring is saturated and comprises from 5 to 8 carbons, that the total number of carbons of the ring and of the radicals R1, R2 and R3 is between 7 and 11 and it being understood that said compound of formula (I) is not: 6-cycloheptylidenehexanal4-(4-methylcyclohexylidene)-butanal4-(4-tert-butylcyclohexylidene)-butanal4-(3,3,5-trimethylcyclohexylidene)-butanal as well as a method of synthesizing said compounds, and their uses in perfumery.
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Page/Page column 11
(2015/06/16)
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- Synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate, components of the sex pheromones of a variety of lepidoptera
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Two simple Wittig procedures for the synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate based on the monoacetylation or monobromination of 1,5-pentanediol were followed.
- Tortajada, Amparo,Mestres, Ramon,Iglesias-Arteaga, Martin A.
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p. 1809 - 1814
(2007/10/03)
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- Synthesis of phytyl- and chroman-derivatized photoaffinity labels based on α-tocopherol
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Photoaffinity analogues of α-tocopherol have been prepared by substituting photosensitive functional groups at either the terminus of an alkyl chain of varying length mimicking the phytyl tail or on C-3 of the chroman portion of tocopherol. The alkyl chain-modified compounds 2a-d contain a hexyl to nonyl alkyl chain extending from C-2 of the chroman, terminating in a tetrafluoroazidobenzyloxy group. These compounds were prepared starting from the commercially available Trolox acid 4, followed by esterification, protection, and reduction to the silyl-protected Trolox aldehyde 7, which was coupled using Wittig chemistry to different ω- hydroxyphosphonium bromides. Reduction of the alkene product, coupling with p-azidotetrafluorobenzyl bromide, and deprotection of the phenolic silyl group gave compounds 2a-d in excellent yields. Chroman-functionalized photoaffinity labels were synthesized starting from the protected tocopherol chromene 16b which was a key intermediate for preparation of a 3-hydroxy derivative, either by reduction of epoxides produced directly with Jacobsen's catalysts or by treatment with NBS in wet DME to give two stereoisomeric bromohydrins which were cyclized and reduced to give the phenol-protected C-3 alcohols 19a,b. These alcohols were then converted to diazoacetate esters, and the protecting group was removed to give 3-diazoacetoxy α-tocopherols 3a,b.
- Lei, Huangshu,Atkinson, Jeffrey
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p. 2560 - 2567
(2007/10/03)
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- Studies on the biomimetic synthesis of the manzamine alkaloids
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The biomimetic synthesis of the manzamine-related alkaloid keramaphidin B is described. The key intramolecular Diels-Alder reaction proposed in the Baldwin and Whitehead hypothesis is demonstrated. An investigation of the modified biomimetic hypothesis pr
- Baldwin,Claridge,Culshaw,Heupel,Lee,Spring,Whitehead
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p. 3154 - 3161
(2007/10/03)
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- A biomimetic approach to the manzamine alkaloids
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Results from model studies of a synthetic approach to the manzamine alkaloids based on a biogenetic theory are reported together with the synthesis of a plausible biogenetic precursor to these alkaloids.
- Baldwin, Jack E.,Claridge, Tim D. W.,Culshaw, Andrew J.,Heupel, Florian A.,Smrckova, Svatava,Whitehead, Roger C.
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p. 6919 - 6922
(2007/10/03)
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