39199-93-4Relevant academic research and scientific papers
Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal
Jette, Carina I.,Tong, Z. Jaron,Hadt, Ryan G.,Stoltz, Brian M.
supporting information, p. 2033 - 2038 (2020/01/02)
Herein, we report a Cu-catalyzed enantioselective allylic alkylation using a γ-butyrolactone-derived silyl ketene acetal. Critical to the development of this work was the identification of a novel mono-picolinamide ligand with the appropriate steric and electronic properties to afford the desired products in high yield (up to 96 %) and high ee (up to 95 %). Aryl, aliphatic, and unsubstituted allylic chlorides bearing a broad range of functionality are well-tolerated. Spectroscopic studies reveal that a CuI species is likely the active catalyst, and DFT calculations suggest ligand sterics play an important role in determining Cu coordination and thus catalyst geometry.
Substrate structural effects in yttrium(III)-catalyzed hydroamination/ cyclizations of 1,2-disubstituted and 1,1,2-trisubstituted aminoalkenes terminated by 2-(phenyl) and 2-(2-heteroarenyl) groups
Jiang, Tao,Huynh, Khoi,Livinghouse, Tom
, p. 193 - 196 (2013/03/13)
A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(1. Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl)furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group. Georg Thieme Verlag Stuttgart · New York.
Asymmetric synthesis of α-chiral allylic silanes by enantioconvergent γ-selective copper(I)-catalyzed Allylic Silylation
Delvos, Lukas B.,Vyas, Devendra J.,Oestreich, Martin
supporting information, p. 4650 - 4653 (2013/06/05)
Gamma way: Regio- and enantioselective allylic substitution with a silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation provides direct access to α-chiral allylic silanes from linear acceptors. The enantioconvergent catalysis employing McQuade's six-membered N-heterocyclic-carbene-copper(I) catalyst is applicable to aryl- and alkyl-substituted allylic phosphates (see scheme). Copyright
Copper- and phosphine-ligand-free palladium-catalyzed direct allylation of electron-deficient polyfluoroarenes with allylic chlorides
Yu, Yan-Bo,Fan, Shilu,Zhang, Xingang
supporting information, p. 14643 - 14648 (2013/01/15)
Simply id(all)ylic: A copper- and phosphine-ligand-free Pd-catalyzed direct allylation of electron-deficient polyfluoroarenes with allylic chlorides and the reaction mechanism are described (see scheme). The simple catalytic system, broad substrate scope,
Kinesin spindle protein (KSP) inhibitors. Part 7: Design and synthesis of 3,3-disubstituted dihydropyrazolobenzoxazines as potent inhibitors of the mitotic kinesin KSP
Garbaccio, Robert M.,Tasber, Edward S.,Neilson, Lou Anne,Coleman, Paul J.,Fraley, Mark E.,Olson, Christy,Bergman, Jeff,Torrent, Maricel,Buser, Carolyn A.,Rickert, Keith,Walsh, Eileen S.,Hamilton, Kelly,Lobell, Robert B.,Tao, Weikang,South, Vicki J.,Diehl, Ronald E.,Davide, Joseph P.,Yan, Youwei,Kuo, Lawrence C.,Li, Chunze,Prueksaritanont, Thomayant,Fernandez-Metzler, Carmen,Mahan, Elizabeth A.,Slaughter, Donald E.,Salata, Joseph J.,Kohl, Nancy E.,Huber, Hans E.,Hartman, George D.
, p. 5671 - 5676 (2008/04/07)
Observations from two structurally related series of KSP inhibitors led to the proposal and discovery of dihydropyrazolobenzoxazines that possess ideal properties for cancer drug development. The synthesis and characterization of this class of inhibitors
MITOTIC KINESIN INHIBITORS
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Page/Page column 47, (2008/06/13)
The present invention relates to tricyclic pyrazoles according to Formula (I) that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also rel
MITOTIC KINESIN INHIBITORS
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Page/Page column 30, (2010/10/20)
The present invention relates to tricyclic pyrazoles according to Formula (III) that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also r
Asymmetric Oxidation of Simple Selenides to Selenoxides in High Enantiopurity. Stereochemical Aspects of the Allyl Selenoxide/Allyl Selenenate Rearrangement
Davis, Franklin A.,Reddy, R. Thimma
, p. 2599 - 2606 (2007/10/02)
For the first time simple alkyl aryl selenoxides of high enantiomeric purity (90-95percent ee) and well-defined stereochemistry are available via the asymmetric oxidation of selenides using (+)- or (-)-N-(phenylsulfonyl)-(3,3-dichlorocamphoryl)oxaziridine heptane-2,3'-oxaziridine>>>.These nonracemic selenoxides, which are more stable in solution than in the solid state, exhibit high configurational stability as long as acid and moisture are excluded.Complete racemization occurs within minutes on addition of trace amounts of acid and water.The asymmetric oxidation of (E)- and (Z)-aryl cinnamyl selenides 11 and 12 with oxaziridine (+)-4 affords optically active 1-phenyl allyl alcohol (15) via a concerted sigmatropic selenoxide-selenenate rearrangement.The extent of 1->3 chirality transfer (41-62percent ee) as well as the endo/exo transition state geometry is highly dependent on the structure of the allylic selenide.
Pyrazolopyrimidine Ribonucleosides as Anticoccidials. 3. Synthesis and Activity of Some Nucleosides of 4-pyrazolopyrimidines
Rideout, Janet L.,Krenitsky, Thomas A.,Chao, Esther Y.,Elion, Gertrude B.,Williams, Raymond B.,Latter, Victoria S.
, p. 1489 - 1494 (2007/10/02)
Ribonucleosides of 4-(alkylthio)-1H-pyrazolopyrimidines have been shown to be useful anticoccidial agents .In that study, the unsaturated 4-allylthio and 4-crotylthio derivatives (19 and 20) were shown to be more active in vivo against Eimeria tenella than their saturated congeners; therefore, some unsaturated (arylalkyl)thio derivatives were synthesized and investigated as anticoccidial agents.The novel compounds in this study (2 to 18) were prepared by the alkylation of 4-mercapto-1-β-D-ribofuranosyl-1H-pyrazolopyrimidine (1), which was prepared by an enzymatic method.The (E)-4-cinnamylthio derivative (2) and the 5'-monophosphate (18) were the most active compounds against E. tenella in vivo.None of the analogues with substituents in the aryl moiety (3 to 13) was more active than 2 in vivo.The geometry about the double bond was important, since the (Z)-4-cinnamylthio derivative (14) was inactive both in vitro and in vivo.The 4-(3-phenylpropynyl)thio and 4-(5-phenyl-2,4-pentadienyl)thio derivatives (15 and 16) were at least as active as 2 in vitro; however, they were less active than 2 in vivo.Compound 2 was effective in vivo against E. tenella, E. necatrix, E. maxima, and E. brunetti; these species of Eimeria were controlled when 2 was given in the diet at levels up to 100 ppm.Infections in vivo due to E. acervulina were controlled by 2 only at about 800 ppm.The broad spectrum of anticoccidial activity shown by 2 represents a significant improvement over the activities reported for related compounds .
