- SYNTHESIS OF (2S,5S)-2, 5-BIS(PHENYLMETHYL)PIPERAZINE BY THE REDUCTION WITH SODIUM BOROHYDRIDE USING TITANIUM TETRACHLORIDE
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Optically active piperazine 1 is synthesized in relatively high yield by the reduction of cyclo-L-Phe-L-Phe with sodium borohydride-titanium tetrachloride
- Soai, Kenso,Hayashi, Hiroshi,Hasegawa, Hitoshi
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- Neochrysosporazines: Precursor-Directed Biosynthesis Defines a Marine-Derived Fungal Natural Product P-Glycoprotein Inhibitory Pharmacophore
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Upregulation of ATP binding cassette (ABC) transporter efflux pumps (i.e. P-glycoprotein, P-gp) can impart multidrug resistance, rendering many chemotherapeutics ineffective and seriously limiting treatment regimes. While ABC transporters remain an attrac
- Capon, Robert J.,Dewa, Amila Agampodi,Elbanna, Ahmed H.,Khalil, Zeinab G.
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- Preventing Candida albicans biofilm formation using aromatic-rich piperazines
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The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm forma
- Simon, Ga?lle,Bérubé, Christopher,Paquet-C?té, Pierre-Alexandre,Grenier, Daniel,Voyer, Normand
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- Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology
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A new ruthenium complex catalyzes the amination of primary and secondary alcohols and the regioselective mono- and sequential diamination of diols via the borrowing hydrogen pathway. Several variations on new intra- and intermolecular cyclizations of aminoalcohols, diols, and diamines lead to heterocyclic ring systems.
- Marichev, Kostiantyn O.,Takacs, James M.
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p. 2205 - 2210
(2016/04/26)
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- Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities
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With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands.
- Bérubé, Christopher,Cardinal, Sébastien,Boudreault, Pierre-Luc,Barbeau, Xavier,Delcey, Nicolas,Giguère, Martin,Gleeton, Dave,Voyer, Normand
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p. 8077 - 8084
(2015/12/30)
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- CHIRAL FLUORINATING REAGENTS
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This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.
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Page/Page column 38
(2014/05/24)
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- Catalytic asymmetric synthesis of substituted morpholines and piperazines
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Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3-substituted morpholines and the diastereoselective synthesis of 2,5-substituted piperazines. Copyright
- Zhai, Huimin,Borzenko, Andrey,Lau, Ying Yin,Ahn, Shin Hye,Schafer, Laurel L.
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supporting information
p. 12219 - 12223
(2013/02/23)
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- Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine-copper(II) complex
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A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral aziridine in few steps.
- Selvakumar, Sermadurai,Sivasankaran, Dhanasekaran,Singh, Vinod K.
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supporting information; experimental part
p. 3156 - 3162
(2011/02/25)
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- Asymmetric Synthesis Using Chiral Piperazine. I. Asymmetric Synthesis of 2-Substituted Alcohol and Carboxylic Acid by Diastereoselective Alkylation of Chiral Diamides Derived from Piperazines
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The diastereoselective alkylation of chiral diamides derived from chiral piperazines afforded optically active alcohols and acids in moderate enantiomeric excesses (up to 68percent e.e.).
- Soai, Kenso,Hayashi, Hiroshi,Shinozaki, Akihiro,Umebayashi, Hideaki,Yamada, Yasuyuki
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p. 3450 - 3452
(2007/10/02)
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- CATALYTIC HYDROGENATION OF 2,5-DIALKYLPYRAZINES AND 3,6-DIALKYL-2-HYDROXYPYRAZINES
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Hydrogenation of several 2,5-dialkylpyrazines and 3,6-dialkyl-2-hydroxypyrazines was achieved in the prersence of platinum oxide.In the former cases, the corresponding trans piperazines were mainly obtained.In the latter cases, the products were further t
- Ohta, Akihiro,Okuwaki, Yukari,Komaru, Tsuyoshi,Hisatome, Mieko,Yoshida, Yasushi,at al.
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p. 2691 - 2701
(2007/10/02)
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- Organic Chemistry of L-Tyrosine. 1. General Synthesis of Chiral Piperazines from Amino Acids
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A new method for the conversion of optically active diketopiperazines (cyclo-dipeptides) into optically pure piperazines is described.Due to poor solubility of certain cyclo-dityrosine derivatives, the usual method using lithium aluminum hydride reaction was problematic, giving racemization under forcing conditions.However, the use of borane/tetrahydrofuran for this diketopiperazine to piperazine reduction proceeded well, affording high yields of optically pure materials.In this manner several mixed cyclo-dityrosine derivatives 9a-d were transformed into the piperazines 10a-d, potentially useful intermediates for the synthesis of the antibiotic alkaloids, piperazinomycin (1) and herquline (2).Finally, the naturally occuring alkaloid isolated from Zanthoxylum arborescens, 7b was prepared by this route.
- Jung, Michael E.,Rohloff, John C.
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p. 4909 - 4913
(2007/10/02)
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