- Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses
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This article describes the synthesis and antiviral activity evaluation of new substituted 1,2,4-oxadiazoles containing a bicyclic substituent at position 5 of the heterocycle and O-acylated amidoximes as precursors for their synthesis. New compounds were
- Borisevich, Sophia S.,Chernyshov, Vladimir V.,Esaulkova, Iana L.,Popadyuk, Irina I.,Salakhutdinov, Nariman F.,Sinegubova, Ekaterina,Yarovaya, Olga I.,Zarubaev, Vladimir V.
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- Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones
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A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,
- Dalinger, Alexander I.,Kalinin, Mikhail A.,Kuranov, Sergey O.,Munkuev, Aldar A.,Okhina, Alina A.,Ottenbacher, Roman V.,Patrusheva, Oxana S.,Ponomarev, Konstantin Y.,Rogachev, Artem D.,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Vatsadze, Sergey Z.,Volcho, Konstantin P.
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- Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones
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The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.
- Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.
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p. 12951 - 12964
(2018/11/30)
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- NOVEL ARYLATED CAMPHENES, PROCESSES FOR THEIR PREPARATION AND USES THEREOF
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The present invention relates to arylated camphenes, processes for their preparation and uses thereof for the manufacture of medicaments for the treatment of diseases, disorders or conditions associated with, or benefiting from stimulation of CB2 receptor
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Page/Page column 34
(2011/06/19)
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- Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones
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Novel chiral Schiff bases were synthesized from (+)-camphor, and their application to asymmetric transfer hydrogenation of prochiral ketones is described. The asymmetric transfer hydrogenation reaction could afford excellent conversion rates (up to 97.3%) and up to 27.3% enantiomeric excess.
- Zhou, Zhongqiang,Bian, Yongjun
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scheme or table
p. 682 - 687
(2010/11/04)
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- Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles
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We have observed a unique reversal in the absolute stereochemistry of the principal adducts from the cycloadditions of camphor-based acylnitroso dienophiles as compared to the adducts obtained through reactions of the corresponding camphor-based chloronitroso compounds.
- Wang, Ying-Chuan,Lu, Tzung-Min,Elango, Shanmugham,Lin, Chao-Kuo,Tsai, Chia-Tzung,Yan, Tu-Hsin
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p. 691 - 695
(2007/10/03)
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- 1,2,3,4-Tetrahydro-1-naphthyl ester as a selective protecting group for carboxylic acids
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The carboxylic acid functionality can be protected as the 1,2,3,4- tetrahydro-1-naphthyl ester, which can be selectively cleaved in the presence of aryl and alkyl esters using chlorotrimethylsilane and sodium iodide in acetonitrile. This protecting group allows room temperature deprotection under essentially neutral conditions throughout the cleavage reaction.
- Slade, Christopher J.,Pringle, Carol A.,Sumner, Ian G.
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p. 5601 - 5604
(2007/10/03)
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- Synthesis and crystal structure of N-[(1S,4R)-2-oxo-pinanyl]-β-alanine methylester
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The title compound, N-[(1S,4R)-2-oxo-pinanyl]-β-alanine methylester, is an important starting material for the electrochemical preparation of chiral amidoalkylation reagents in the synthesis of chiral β-substituted β-amino acid derivatives. The investigation of its crystal structure reveals an arrangement of the carbonyl group and the amine function, which is influenced by a hydrogen bonding interaction. This conformation makes the molecule especially appropriate for further synthetical modification.
- Albert, Barbara,Jansen, Martin,Jakobi, Joerg,Steckhan, Eberhard
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p. 1188 - 1190
(2007/10/03)
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- Synthesis of several novel optically active nitroxyl radicals
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Optically active nitroxyl radicals are prepared from enantiomerically pure bicyclic tempenoids. (-)-Camphoxyl radical (-)-4 derived from commercially available oxazolidinone (-)-1 and (+)-camphoxyl radical (+)-4 derived from (-)-camphene are readily prepared, conformationally rigid, enantiomeric nitroxyl radicals. (-)-Camphorsulphonic acid is used to prepare two additional optically active nitroxyl radicals 9 and 12.
- Braslau, Rebecca,Kuhn, Heiko,Burrill II, Leland C.,Lanham, Kenneth,Stenland, Chris J.
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p. 7933 - 7936
(2007/10/03)
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- Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
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Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.
- Brungs,Danielmeier,Jakobi,Nothhelfer,Stahl,Zietlow,Steckhan
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p. 575 - 590
(2007/10/03)
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- ENANTIOSELECTIVE SYNTHESIS OF SEC-ALLYLALCOHOLS BY CATALYTIC ASYMMETRIC ADDITION OF DIVINYLZINC TO ALDEHYDES.
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Readily available chiral tridentate ligand 8 catalyzes the highly Si-face selective addition of diethyl-, di-n-propylzinc and, more significantly, of divinylzinc to aromatic and aliphatic aldehydes whereas bidentate ligands 11 and 12 exert a topologically reversed catalytic bias.
- Oppolzer, Wolfgang,Radinov, Rumen N.
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p. 5645 - 5648
(2007/10/02)
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- Method for preparing 10,10-difluoro prostacyclin intermediates and new compounds produced thereby
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A method is provided for preparing intermediates for use in 10,10-difluoro prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate STR1 and subjecting same to a Wittig reaction to form the difluoro dihydroxy prostacyclin intermediate STR2 All of the above-mentioned intermediates are novel compounds and thus are also provided.
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