ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 3
BKCSDE 31(3)
March 20, 2010 

539  

Synthesis of N,N-Bis(nonaflyl) Squaric Acid Diamide and its Application to Organic Reactions
Cheol Hong Cheon, Hisashi Yamamoto*
Keywords: Brønsted acid catalysis, Squaric acid, Mukaiyama Michael reaction, Carbonyl ene reaction
DOI: https://doi.org/10.5012/bkcs.2010.31.3.539

Abstract | Full Text: PDF

541  

3-Isoxazolidinone: A New Achiral Template for Enantioselective Transformations
Mukund P Sibi*, Brandon Gustafson, Julien Coulomb
Keywords: Achiral template, 3-Isoxazolidinone, Diels-Alder, Rotamer control, Chiral Lewis acid
DOI: https://doi.org/10.5012/bkcs.2010.31.3.541

Abstract | Full Text: PDF

543  

A Convenient, High Yielding Cleavage of the Thiocarbonyl Group in Xanthates
Beatrice Quiclet Sire*, Samir Z Zard*
Keywords: Xanthates, Ozonolysis, Thiolcarbonates, RAFT polymers
DOI: https://doi.org/10.5012/bkcs.2010.31.3.543

Abstract | Full Text: PDF

545  

Stannylcarbonylation of Hydroxy-substituted Alkynes. Intramoleuclar Trapping of α-Ketenyl Radicals by a Hydroxy Group Leading to Lactols
Ilhyong Ryu*, Takahide Fukuyama, Osamu Nobuta, Yoshitaka Uenoyama
Keywords: Radical carbonylation, α-Ketenyl radicals, Lactols, Carbon monoxide, Tin radical
DOI: https://doi.org/10.5012/bkcs.2010.31.3.545

Abstract | Full Text: PDF

547  

Chemoselective Oxidation of Sulfides Promoted by a Tightly Convoluted Polypyridinium Phosphotungstate Catalyst with H₂O₂
Chung Keun Jin, Yoichi M A Yamada, Yasuhiro Uozumi
Keywords: Polymer-supported catalyst, Tungsten, Oxidation, Sulfide, Sulfone
DOI: https://doi.org/10.5012/bkcs.2010.31.3.547

Abstract | Full Text: PDF

549  

Synthesis of Nucleoside-based Phospholipid Amphiphiles
Hun Rok Jung, Tran Khac Vu, Seung Kyu Choi, Sun Min Park, Byeang Hyean Kim*
Keywords: Nucleoside, Phospholipids, Self-assembly
DOI: https://doi.org/10.5012/bkcs.2010.31.3.549

Abstract | Full Text: PDF

551  

Ligandless Copper-Catalyzed β-Boration of α,β-Unsaturated Compounds in Aqueous Solution
Heesung Chea, Hak Suk Sim, Jaesook Yun
Keywords: Boration, Copper, Diboron, α,β-Unsaturated carbonyl compounds
DOI: https://doi.org/10.5012/bkcs.2010.31.3.551

Abstract | Full Text: PDF

553  

Synthesis of 1,3-Oxazolidines and 1,2-Amino Alcohols from N-Tosylimines Using Rh(II) Catalyst in Acetone
Nam Sun Kim, Se Youn Kang, Seung Han Lee
Keywords: Oxazolidine, Amino alcohol, Carbonyl ylide, Rh(II) catalyst, Multi-component reaction
DOI: https://doi.org/10.5012/bkcs.2010.31.3.553

Abstract | Full Text: PDF

555  

Synthesis of Ophiocerins from Non-Carbohydrate Sources
Huijeong Hong, Dong Min Lee, Han Young Kang
Keywords: Ophiocerin, Total synthesis, Stereoselective synthesis, Tetrahydropyran, Natural pro
DOI: https://doi.org/10.5012/bkcs.2010.31.3.555

Abstract | Full Text: PDF

557  

Construction of the ABC-ring System of Delnudine through Free Radical Cyclization and Alkylidene Carbene C-H Insertion
Sejin Lee, Hee Yoon Lee
Keywords: Free radical, Tandem cyclization, C-H Insertion, Natural product, Delnudine
DOI: https://doi.org/10.5012/bkcs.2010.31.3.557

Abstract | Full Text: PDF

559  

Intramolecular Carbocyclization of Allenoate-aldehydes with Hexamethylditin Catalyzed by Palladium Complex: Synthesis of Cyclic Dienes
Wonjae Seong, Suyeon Gong, Seok Hoon Woo, Chan Mo Yu*
Keywords: Allenoate, Carbocyclization, Diene, Lactone, Palladium
DOI: https://doi.org/10.5012/bkcs.2010.31.3.559

Abstract | Full Text: PDF

561  

Synthesis of Benzofuran Chains: Monomer to Tetramer
Jae min Suk, Kyu Sung Jeong*
Keywords: Foldamer, Benzofuran, Binding, Helix
DOI: https://doi.org/10.5012/bkcs.2010.31.3.561

Abstract | Full Text: PDF

563  

Synthesis of 2,5-Disubstituted Pyrrolidines from N-Alkenyl and Alkynyl N-Benzoyloxysulfonamides Catalyzed by (CuOTf)₂C₆H₆
Wei Min Liu, Zhen Hong Liu, Wei Wen Cheong, Lu Yi Teo Priscilla, Yongxin Li, Koichi Narasaka*
Keywords: Pyrrolidines, Intramolecular radical cyclization, Copper catalyst, N-Benzoyloxysulfonamides
DOI: https://doi.org/10.5012/bkcs.2010.31.3.563

Abstract | Full Text: PDF

570  

Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides Akinori Sato, Hideki Yorimitsu,* and Koichiro Oshima*
A variety of ynamides undergo highly regio , stereoselective radical addition of arenethiols with the aid of triethylborane as a radical initiator The products, N [(Z) 2 arylsulfanyl 1 alkenyl]amides, can be reduced with triethylsilane in trifluoroacetic
Keywords: Radical addition, Hydrothiolation, Ynamide, Hydrogenation
DOI: https://doi.org/10.5012/bkcs.2010.31.3.570

Abstract | Full Text: PDF

577  

Synthesis and Characterization of Highly Fluorescent and Thermally Stable π-Conjugates involving Spiro[fluorene-9,4’-[4H]indeno[1,2-b]furan]
Toshiyuki Kowada, Kouichi Ohe*
Keywords: Fluorescence, Spiro compounds, Cross-coupling, Palladium
DOI: https://doi.org/10.5012/bkcs.2010.31.3.577

Abstract | Full Text: PDF

582  

Rhodium-Catalyzed Reductive Decyanation of Nitriles Using Hydrosilane as a Reducing Agent: Scope, Mechanism and Synthetic Application
Mamoru Tobisu*, Ryo Nakamura, Yusuke Kita, Naoto Chatani*
Keywords: Reductive decyanation, Carbon-carbon bond activation, Rhodium catalyst, Hydrosilane
DOI: https://doi.org/10.5012/bkcs.2010.31.3.582

Abstract | Full Text: PDF

588  

Design and Synthesis of Resin-Conjugated Tamiflu Analogs for Affinity Chromatography
Yasuaki Kimura, Kenzo Yamatsugu, Motomu Kanai*, Noriko Echigo, Takashi Kuzuhara, Masakatsu Shibasaki*
Keywords: Tamiflu, Immobilization, Affinity chromatography, Abnormal behavior, Neuraminidase
DOI: https://doi.org/10.5012/bkcs.2010.31.3.588

Abstract | Full Text: PDF

595  

Reactions of Acetyl Radical with Acetylene ? A Computational Study Tu Anh Tran, Carl H. Schiesser*
Ab initio, DFT molecular orbital calculations predict that acetyl radical reacts with acetylene through interactions primarily involving the SOMO of the radical, the in plane π bond of acetylene An energy barrier (ΔE1) of 39.6 kJ mol¹ is predic
Keywords: Acetyl radical, Acetylene, Molecular orbital calculations
DOI: https://doi.org/10.5012/bkcs.2010.31.3.595

Abstract | Full Text: PDF

599  

Detection of Near-membrane Calcium Ions in Live Tissues with a Two-Photon Fluorescent Probe
Yu Na Shin, Chang Su Lim, Yu Shun Tian, Won Young Rho, Bong Rae Cho*
Keywords: Calcium, Live tissue, Two-photon microscopy, Two-photon probe
DOI: https://doi.org/10.5012/bkcs.2010.31.3.599

Abstract | Full Text: PDF

606  

Molecular Docking Study of Aminoacyl-tRNA Synthetases with Ligand Molecules from Four Different Scaffolds
Nagakumar Bharatham, Kavitha Bharatham,Yuno Lee, Songmi Kim, Prettina Lazar, Ayoung Baek, Chanin Park, Heesung Eum, Hyun Joon Ha, Sae Young Yun, Won Koo Lee, Sunghoon Kim, Keun Woo Lee*
Keywords: aaRS (aminoacyl-tRNA synthetase), HisRS, IleRS, Antibacterial drug target, Molecular docking simulation
DOI: https://doi.org/10.5012/bkcs.2010.31.3.606

Abstract | Full Text: PDF

611  

Synthesis of Substituted Imidazolidin-2-ones as Aminoacyl-tRNA Synthase Inhibitors
Heesung Eum, Yuno Lee, a Songmi Kim, Ayoung Baek, Minky Son, Keun Woo Lee, Seung Whan Ko, Sunghoon Kim, Sae Young Yun, Won Koo Lee, Hyun Joon Ha*
Keywords: Aminoacyl-tRNA synthase inhibitors, Imidazolidin-2-ones
DOI: https://doi.org/10.5012/bkcs.2010.31.3.611

Abstract | Full Text: PDF

615  

Fluorescence Sensing Properties of Thiazolobenzo-crown Ether Incorporating Coumarin
Sang Hoon Lee, Aasif Helal, Hong Seok Kim*
Keywords: Thiazolobenzo-crown ether, Coumarin, Fluorescence sensor, Mercury ion
DOI: https://doi.org/10.5012/bkcs.2010.31.3.615

Abstract | Full Text: PDF

620  

Separation of the Enantiomers of β-Blockers Using Brush Type Chiral Stationary Phase Derived from Conformationally Rigid α-Amino β-Lactam
William H Pirkle, Wonjae Lee*
Keywords: Enantiomer separation, β-Blockers, Chiral stationary phase
DOI: https://doi.org/10.5012/bkcs.2010.31.3.620

Abstract | Full Text: PDF

624  

A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Iodide Ion
Jong Seung Kim*, Sun Young Park, Sang Hoon Kim, Pierre Thuery, Rachid Souane, Susan E Matthews*, Jacques Vicens*
Keywords: 1,2,3-Triazole, Calixarenes, Fluorescent sensors, Anion sensing, Iodide
DOI: https://doi.org/10.5012/bkcs.2010.31.3.624

Abstract | Full Text: PDF

630  

Calix[4]pyrroles Bearing Pyrene-pickets at Diametrical Meso-positions with Amide Linkage
Jaeduk Yoo, In won Park, Tae Young Kim, Chang Hee Lee*
Keywords: Calix[4]pyrrole, Fluorophore appended, Chemosensors, Pyrene, CHEF
DOI: https://doi.org/10.5012/bkcs.2010.31.3.630

Abstract | Full Text: PDF

635  

A New Approch for Catalyst Optimization: Host/Guest Complexes of Chiral Bisphosphine Bearing Imidazolidinone and Their Application in Rh-Catalyzed Asymmetric Hydrogenation
Jung Hwan Park, Hyunik Shin, Doo Han Park, Sang gi Lee
Keywords: Chiral catalyst, Catalyst optimization, Host/guest
DOI: https://doi.org/10.5012/bkcs.2010.31.3.635

Abstract | Full Text: PDF

639  

Supramolecular Micelle from Amphiphilic Mn(III)-porphyrin Derivatives as a Potential MRI Contrast Agent
Kwangmo Choi, Do Hyung Lee, Woo Dong Jang*
Keywords: Porphyrin, Self-assembly, Micelle, MRI
DOI: https://doi.org/10.5012/bkcs.2010.31.3.639

Abstract | Full Text: PDF

645  

Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide
Dahan Eom, Sung Hong Kim, Phil Ho Lee*
Keywords: Allenol, 2-Halo-1,3-diene, Indium trihalide, Selectivity
DOI: https://doi.org/10.5012/bkcs.2010.31.3.645

Abstract | Full Text: PDF

650  

Immobilization of Lipase on Single Walled Carbon Nanotubes in Ionic Liquid
Han Ki Lee, Jae Kwan Lee, Mahn Joo Kim*, Cheol Jin Lee
Keywords: Lipase, Single walled carbon nanotube, Immobilization, Ionic liquid, Biocatalysis
DOI: https://doi.org/10.5012/bkcs.2010.31.3.650

Abstract | Full Text: PDF

653  

Enantioselective Total Synthesis of (-)-Clavosolide A and B
Jung Beom Son, Si Nae Kim, Na Yeong Kim, Min ho Hwang, Wonsun Lee, Duck Hyung Lee*
Keywords: Enantioselective total synthesis, Clavosolide A, Clavosolide B
DOI: https://doi.org/10.5012/bkcs.2010.31.3.653

Abstract | Full Text: PDF

664  

New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives
Likai Xia, Manchala Narasimhulu, Xin Li, Jae Jin Shim, Yong Rok Lee*
Keywords: Geranylated acetophenone, Melicope semecarpifolia, Chalcone
DOI: https://doi.org/10.5012/bkcs.2010.31.3.664

Abstract | Full Text: PDF

670  

Synthesis of Cyclohexene Derivatives from 1,5-Enynes via Gold-Catalysis and Iodocyclization: A Comparative Study and Applications
in the Synthesis of 7/5 or 8/5 Fused Rings, Biaryls
DOI: https://doi.org/10.5012/bkcs.2010.31.3.670

Abstract | Full Text: PDF

678  

Liquid Chromatographic Resolution of Tocainide and Its Analogues on a Doubly Tethered Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid
Hee Jin Kim, Hee Jung Choi, Myung Ho Hyun*
Keywords: Chiral stationary phase, Enantiomer separation, Liquid chromatography, (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid, Tocainide
DOI: https://doi.org/10.5012/bkcs.2010.31.3.678

Abstract | Full Text: PDF

683  

Gold-Catalyzed Cycloisomerization of (2-Alkynyl-1-cycloalkenyl)methanols to Highly Substituted Furans
Chang Ho Oh*, Hyun Jik Yi, Kyu Hwan Lee
Keywords: Gold catalysis, Furan, Cyclization, Alkynol
DOI: https://doi.org/10.5012/bkcs.2010.31.3.683

Abstract | Full Text: PDF

689  

Kinetics and Mechanism of Nucleophilic Displacement Reactions of Y-Substituted Phenyl Benzoates with Cyanide Ion
Song I Kim, Eun Hee Kim, Ik Hwan Um*
Keywords: Aryl benzoates, Brønsted-type plot, Hammett plot, Rate-determining step, Yukawa-Tsuno plot
DOI: https://doi.org/10.5012/bkcs.2010.31.3.689

Abstract | Full Text: PDF

694  

Catalytic Asymmetric Construction of the exo-7-Aryl-6,8-dioxabicyclo[3.2.1]octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy
Yasunobu Kurosaki, Naoyuki Shimada, Masahiro Anada, Hisanori Nambu, Shunichi Hashimoto
Keywords: Asymmetric reaction, 1,3-Dipolar cycloaddition, Carbonyl ylides, Chiral dirhodium(II) carboxylates, Aldehydes
DOI: https://doi.org/10.5012/bkcs.2010.31.3.694

Abstract | Full Text: PDF

697  

Synthesis of Ruthenium Pentamethyl[60]fullerene Complexes Bearing Monodentate Diphenylphosphino-methane, -ferrocene, and -butane Ligands
Yutaka Matsuo*, Bo Keun Park, Yuichi Mitani, Yu Wu Zhong, Masashi Maruyama, Eiichi Nakamura
Keywords: Fullerenes, Ruthenium, Phosphine ligands, Monodentate ligands
DOI: https://doi.org/10.5012/bkcs.2010.31.3.697

Abstract | Full Text: PDF

700  

Facile Synthesis of N-Tosyl Aza-Baylis-Hillman Adducts of Acrylamide via a Pd-Catalyzed Hydration of Nitrile to Amide
Eun Sun Kim, Yu Mi Kim, Jae Nyoung Kim
Keywords: N-Tosyl aza-Baylis-Hillman adducts, Palladium, Nitrile, Hydration, Amide
DOI: https://doi.org/10.5012/bkcs.2010.31.3.700

Abstract | Full Text: PDF

704  

Synergistic Effect of Pd(II) and Acid Catalysts on Tandem Annulation Reaction for the Regioselective Synthesis of Ring-Fused Quinolines
Su Kyung Ock, So Won Youn*
Keywords: Tandem annulation reaction, Quinolines, Pd(OAc)₂, p-TsOH
DOI: https://doi.org/10.5012/bkcs.2010.31.3.704

Abstract | Full Text: PDF

708  

Synthesis of 10-Arylanthracenes from 2-Fluorobenzophenones and Arylacetonitriles via a One-Pot SNAr and Anionic Cyclization Cascade
Sung Hwan Kim, Se Hee Kim, Ko Hoon Kim, Jae Nyoung Kim*
Keywords: 10-Arylanthracenes, SNAr, Anionic cyclization, Arylacetonitriles
DOI: https://doi.org/10.5012/bkcs.2010.31.3.708

Abstract | Full Text: PDF

712  

Isothiouronium Salts Based on Anthracene and Pyrene as Anion Sensors
Quynh Pham Bao Nguyenm, Taek Hyeon Kim*
Keywords: Isothiouronium salts, Isomerism, Anion sensing
DOI: https://doi.org/10.5012/bkcs.2010.31.3.712

Abstract | Full Text: PDF

716  

Fluorescent Chemosensor for Detection of PPi Through the Inhibition of Excimer Emission in Water
Soon Young Kim, Jong In Hong*
Keywords: Fluorescent chemosensor, Pyrophosphate, Pyrene, Excimer, Photoinduced Electron Transfer
DOI: https://doi.org/10.5012/bkcs.2010.31.3.716

Abstract | Full Text: PDF

720  

Stereoselective α-Sialylation with Sialyl Pentenoates as Donors and PhSeOTf as the Activator
Bo Young Lee, Young Kil Chang, Dae Hwan Suk, Kwan Soo Kim*
Keywords: Glycosyl pentenoate, α-Sialylation, Glycosylation, Phenylselenyl triflate
DOI: https://doi.org/10.5012/bkcs.2010.31.3.720

Abstract | Full Text: PDF

724  

Chiral Discrimination of α-Chiral Ammonium Ions by Sterically Geared Chiral Tripodal Oxazolines
Sung Gon Kim, Sunderraman Sambasivan, Kyo Han Ahn*
Keywords: Chiral discrimination, Organoammonium ions, Preorganization, Tripodal oxazolines
DOI: https://doi.org/10.5012/bkcs.2010.31.3.724

Abstract | Full Text: PDF

727  

Highly Efficient Synthesis of (+)-Bromoxone, (+)-Epiepoxydon and (+)-Epiepoformin
Ming Yu Jin, Geum Sook Hwang, Hee Il Chae, Sun Hee Jung, Do Hyun Ryu*
Keywords: Epoxyquinol, Diels-Alder cycloaddition, Enantioselective catalysis, Epoxidation
DOI: https://doi.org/10.5012/bkcs.2010.31.3.727

Abstract | Full Text: PDF

731  

Photoinduced Rearrangement Reaction of 2-(Pentamethyldisilanyloxymethyl) phenylpentamethyldisilane
Seung Ki Park*, Su Yeon Gong
Keywords: 2-(Pentamethyldisilanyloxymethyl)phenylpentamethyldisilane, Disilane
DOI: https://doi.org/10.5012/bkcs.2010.31.3.731

Abstract | Full Text: PDF

735  

Use of an Ionic Liquid as a Co-solvent for Recyclable Pd/C-mediated N-Debenzylation
Jin Kyu Choi, Byung Sun Jeon, Jong Hyun Cho, B Moon Kim*
Keywords: Pd/C, N-Debenzylation, Co-solvent, Ionic liquid, Recycling
DOI: https://doi.org/10.5012/bkcs.2010.31.3.735

Abstract | Full Text: PDF

739  

A New Diarylpropane from the Stem Bark of Lindera erythrocarpa Makino
Ryeo Kyeong Ko, Min Chul Kang, Yeon Jun Jin, Ho Min Choi, Bong Seok Kim, Jong Heon Han, Gi Ok Kim, Nam Ho Lee
Keywords: Lindera erythrocarpa, Lauraceae, Diarylpropane, Kanakugiol
DOI: https://doi.org/10.5012/bkcs.2010.31.3.739

Abstract | Full Text: PDF

742  

Synthesis of (E)-α-Ethynyl-α,β-unsaturated Esters from Allenyl Acetates Catalyzed by DABCO and Their Application to Sonogashira Cross-Coupling Reactions
Hyunseok Kim, Doosup Shin, Kwangmoo Lee, Sangkyu Lee, Sanghyuk Kim, Phil Ho Lee*
Keywords: Allenyl acetate, Catalysis, Enyne, (E)-α-Ethynyl-α,β-unsaturated ester, DABCO
DOI: https://doi.org/10.5012/bkcs.2010.31.3.742

Abstract | Full Text: PDF

746  

Metal-Free Conversion of Carboxamides to Ureas Using Tertiary Amines and Iodosylmesitylene
Hoon Han, Sukbok Chang*
Keywords: Ureas, Amides, Curtius rearrangement, N-Dealkylaton, Iodosylmesitylene
DOI: https://doi.org/10.5012/bkcs.2010.31.3.746

Abstract | Full Text: PDF

749  

6-Methyl-2,4-pyrimidyl Diesters. A Highly Efficient Acylating Agent for the Synthesis of Unsymmetrical Ketones
Jae In Lee
Keywords: 6-Methyl-2,4-pyrimidyl diesters, Acylating agents, Ketones, Substitution
DOI: https://doi.org/10.5012/bkcs.2010.31.3.749

Abstract | Full Text: PDF

753  

Thickness Control of Biomimetic Silica Thin Films:Grafting Density of Poly(2-(dimethylamino)ethyl methacrylate) Templates
Sung Ho Yang, Insung S Choi*
Keywords: Biomimicry, Grafting density, Mixed self-assembled monolayers, Silica, Silicification
DOI: https://doi.org/10.5012/bkcs.2010.31.3.753

Abstract | Full Text: PDF