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Original contributions reporting novel, important findings of fundamental research in all branches of the theory and practice of organic and bioorganic chemistry.

Editors: C. Dale Poulter & Associate Editors
Volume: 73, 24 issues

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Vol. 73, No. 10: May 16, 2008
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PERSPECTIVE
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Physical Organic Chemistry on the Brain
Dennis A. Dougherty
pp 3667 - 3673; (Perspective) DOI: 10.1021/jo8001722
Abstract   Full:  HTML /  PDF (296K) 

FEATURED ARTICLES
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Cyclic Nitriles: Stereodivergent Addition−Alkylation−Cyclization to cis- and trans-Abietanes
Fraser F. Fleming, Guoqing Wei, and Omar W. Steward
pp 3674 - 3679; (Featured Article) DOI: 10.1021/jo8001062
Abstract   Full:  HTML /  PDF (887K)  Supporting Info 

ARTICLES
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Density Functional Theory Studies of Negishi Alkyl–Alkyl Cross-Coupling Reactions Catalyzed by a Methylterpyridyl-Ni(I) Complex
Xufeng Lin and David Lee Phillips
pp 3680 - 3688; (Article) DOI: 10.1021/jo702497p
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Design of a “New Motif” with β-Amino Acids and α-Aminoxy Acids: Synthesis of Hybrid Peptides with 12/10-Helix
Gangavaram V. M. Sharma, Vennampalli Manohar, Samit K. Dutta, Velaparthi Subash, and Ajit C. Kunwar
pp 3689 - 3698; (Article) DOI: 10.1021/jo702242q
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Phorbasides A−E, Cytotoxic Chlorocyclopropane Macrolide Glycosides from the Marine Sponge Phorbas sp. CD Determination of C-Methyl Sugar Configurations
John B. MacMillan, Guang Xiong-Zhou, Colin K. Skepper, and Tadeusz F. Molinski
pp 3699 - 3706; (Article) DOI: 10.1021/jo702307t
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A Novel Polymer Supported Approach to Nucleoside Modification
Suyeal Bae and Mahesh K. Lakshman
pp 3707 - 3713; (Article) DOI: 10.1021/jo702558n
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Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase
Andrew Plant, Peter Thompson, and David M. Williams
pp 3714 - 3724; (Article) DOI: 10.1021/jo702564y
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New Telluride-Mediated Elimination for Novel Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides
Jia Sheng, Abdalla E. A. Hassan, and Zhen Huang
pp 3725 - 3729; (Article) DOI: 10.1021/jo7025806
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Kinetics and Mechanism of Large Rate Enhancement in the Alkaline Hydrolysis of N′-Morpholino-N-(2′-methoxyphenyl)phthalamide
Yoke-Leng Sim, Azhar Ariffin, and M. Niyaz Khan
pp 3730 - 3737; (Article) DOI: 10.1021/jo702695k
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Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1H-tetrazoles
Helmut Quast and Lothar W. Bieber
pp 3738 - 3744; (Article) DOI: 10.1021/jo702697f
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Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals
Patricia Martínez-Bescos, Fernando Cagide-Fagín, Luis F. Roa, Juan Carlos Ortiz-Lara, Krzysztof Kierus, Lidia Ozores-Viturro, Marta Fernández-González, and Ricardo Alonso
pp 3745 - 3753; (Article) DOI: 10.1021/jo702731b
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A Cross-Metathesis Route to the 5-F2-Isoprostanes
Bhaumik A. Pandya and Marc L. Snapper
pp 3754 - 3758; (Article) DOI: 10.1021/jo702702s
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Taking Advantage of the Radical Character of Tris(2,4,6-trichlorophenyl)methyl To Synthesize New Paramagnetic Glassy Molecular Materials
Sonia Castellanos, Dolores Velasco, Francisco López-Calahorra, Enric Brillas, and Luis Julia
pp 3759 - 3767; (Article) DOI: 10.1021/jo702723k
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Application of 2-Pyridyl-Substituted Hemithioindigo as a Molecular Switch in Hydrogen-Bonded Porphyrins
Kiyoshi Tanaka, Kiyoshi Kohayakawa, Satoru Iwata, and Takayuki Irie
pp 3768 - 3774; (Article) DOI: 10.1021/jo800091d
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A Host-Induced Intramolecular Charge-Transfer Complex and Light-Driven Radical Cation Formation of a Molecular Triad with Cucurbit[8]uril
Dapeng Zou, Samir Andersson, Rong Zhang, Shiguo Sun, Björn Åkermark, and Licheng Sun
pp 3775 - 3783; (Article) DOI: 10.1021/jo800110b
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N,Nʼ-Disubstituted Methylenediimidazolium Salts: A Versatile Guest for Various Macrocycles
Nadim Noujeim, Loı̈c Leclercq, and Andreea R. Schmitzer
pp 3784 - 3790; (Article) DOI: 10.1021/jo702683c
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Starburst Triarylamine Based Dyes for Efficient Dye-Sensitized Solar Cells
Zhijun Ning, Qiong Zhang, Wenjun Wu, Hongcui Pei, Bo Liu, and He Tian
pp 3791 - 3797; (Article) DOI: 10.1021/jo800159t
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Modular Synthesis of 5-Substituted Thiophen-2-yl C-2′-Deoxyribonucleosides
Jan Bárta, Radek Pohl, Blanka Klepetářová, Nikolaus P. Ernsting, and Michal Hocek
pp 3798 - 3806; (Article) DOI: 10.1021/jo800177y
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A Convenient Route to N-[2-(Fmoc)aminoethyl]glycine Esters and PNA Oligomerization Using a Bis-N-Boc Nucleobase Protecting Group Strategy
Filip Wojciechowski and Robert H. E. Hudson
pp 3807 - 3816; (Article) DOI: 10.1021/jo800195j
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Total Synthesis and Determination of Relative and Absolute Configuration of Multiplolide A
C. V. Ramana, Tushar P. Khaladkar, Soumitra Chatterjee, and Mukund K. Gurjar
pp 3817 - 3822; (Article) DOI: 10.1021/jo7027568
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Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones
Samir K. Mandal, Moumita Paira, and Subhas C. Roy
pp 3823 - 3827; (Article) DOI: 10.1021/jo800049p
Abstract   Full:  HTML /  PDF (221K)  Supporting Info 
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CrCl2-Promoted Stereospecific and Stereoselective Alkyl- and Silylcyclopropanation of α,β-Unsaturated Amides
José M. Concellón, Humberto Rodríguez-Solla, Carmen Méjica, Elena G. Blanco, Santiago García-Granda, and M. Rosario Díaz
pp 3828 - 3836; (Article) DOI: 10.1021/jo800103t
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New Insight into Ni(II)-Catalyzed Cyclization Reactions of Propargylic Compounds with Soft Nucleophiles: Novel Indenes Formation
Fa-Rong Gou, Hai-Peng Bi, Li-Na Guo, Zheng-Hui Guan, Xue-Yuan Liu, and Yong-Min Liang
pp 3837 - 3841; (Article) DOI: 10.1021/jo800155a
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CeCl3·7H2O: An Effective Additive in Ru-Catalyzed Enantioselective Hydrogenation of Aromatic α-Ketoesters
Qinghua Meng, Yanhui Sun, Virginie Ratovelomanana-Vidal, Jean Pierre Genêt, and Zhaoguo Zhang
pp 3842 - 3847; (Article) DOI: 10.1021/jo800228e
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Using Molecular Iodine in Direct Oxidative Condensation of Aldoses with Diamines: An Improved Synthesis of Aldo-benzimidazoles and Aldo-naphthimidazoles for Carbohydrate Analysis
Chunchi Lin, Po-Ting Lai, Sylvain Kuo-Shiang Liao, Wei-Ting Hung, Wen-Bin Yang, and Jim-Min Fang
pp 3848 - 3853; (Article) DOI: 10.1021/jo800234x
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Preparation of Nonsymmetrically Substituted Stilbenes in a One-Pot Two-Step Heck Strategy Using Ethene As a Reagent
Chad M. Kormos and Nicholas E. Leadbeater
pp 3854 - 3858; (Article) DOI: 10.1021/jo800235c
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Unsymmetric Pyrrole, Thiophene, and Furan-Conjugated Comonomers Prepared Using Azomethine Connections: Potential New Monomers for Alternating Homocoupled Products
Stéphane Dufresne and W. G. Skene
pp 3859 - 3866; (Article) DOI: 10.1021/jo8002503
Abstract   Full:  HTML /  PDF (744K)  Supporting Info 
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Efficient Synthesis of cis- and trans-3,4-Dihydroxy-3,4-dihydromollugin
Naga Venkata Sastry Mudiganti, Sven Claessens, Pascal Habonimana, and Norbert De Kimpe
pp 3867 - 3874; (Article) DOI: 10.1021/jo800312j
Abstract   Full:  HTML /  PDF (251K)  Supporting Info 
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Linker-Oriented Design of Binaphthol Derivatives for Optical Resolution Using Lipase-Catalyzed Reaction
Tomohiro Taniguchi, Taka-aki Fukuba, Shuhei Nakatsuka, Shuichi Hayase, Motoi Kawatsura, Hidemitsu Uno, and Toshiyuki Itoh
pp 3875 - 3884; (Article) DOI: 10.1021/jo800351h
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Functionalization of Organotrifluoroborates: Reductive Amination
Gary A. Molander and David J. Cooper
pp 3885 - 3891; (Article) DOI: 10.1021/jo800383e
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One-Step Synthesis of Low Molecular Weight Poly(p-phenyleneethynylenevinylene)s via Polyaddition of Aromatic Diynes by Catalysis of the [Ru(p-cymene)Cl2]2/AcOH System
Chiara Pasquini, Ilaria Fratoddi, Donatella Capitani, Luisa Mannina, and Mauro Bassetti
pp 3892 - 3899; (Article) DOI: 10.1021/jo800471p
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A New Cyclization to Fused Pyrazoles Tunable for Pericyclic or Pseudopericyclic Route: An Experimental and Theoretical Study
László Filák, Tibor András Rokob, Gyöngyvér Ágnes Vaskó, Orsolya Egyed, Ágnes Gömöry, Zsuzsanna Riedl, and György Hajós
pp 3900 - 3906; (Article) DOI: 10.1021/jo800483a
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NOTES
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2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl)]-1,3,2-dioxaphospholane: A Practical Chiral Pool-Derived Reagent for Determining Enantiomeric Purity of Alcohols
Matthias Amberg, Uwe Bergsträsser, Georg Stapf, and Jens Hartung
pp 3907 - 3910; (Note) DOI: 10.1021/jo7026068
Abstract   Full:  HTML /  PDF (339K)  Supporting Info 
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Synthesis, Structure, and Metal Complexation Behavior of a New Type of Functionalized Chiral Phenanthroline Derivative
Jacob M. Plummer, Jeremy A. Weitgenant, Bruce C. Noll, Joseph W. Lauher, Olaf Wiest, and Paul Helquist
pp 3911 - 3914; (Note) DOI: 10.1021/jo702566m
Abstract   Full:  HTML /  PDF (751K)  Supporting Info 
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A Carbohydrate-Based Approach for the Total Synthesis of Aculeatin D and 6-epi-Aculeatin D
C. V. Ramana and Burgula Srinivas
pp 3915 - 3918; (Note) DOI: 10.1021/jo800026n
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A Convenient Method for the Assignment of Relative Configuration of Acyclic α-Alkyl-β-hydroxy Carbonyl Compounds by 1H NMR
Dimitris Kalaitzakis and Ioulia Smonou
pp 3919 - 3921; (Note) DOI: 10.1021/jo800066a
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Indium−Copper and Indium−Silver Mediated Barbier–Grignard-Type Alkylation Reaction of Aldehydes Using Unactivated Alkyl Halides in Water
Zhi-Liang Shen, Yan-Lin Yeo, and Teck-Peng Loh
pp 3922 - 3924; (Note) DOI: 10.1021/jo8000589
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A Novel One-Pot Pseudo-Five-Component Synthesis of 4,5,6,7-Tetrahydro-1H-1,4-diazepine-5-carboxamide Derivatives
Ahmad Shaabani, Ali Maleki, Hamid Mofakham, and Jafar Moghimi-Rad
pp 3925 - 3927; (Note) DOI: 10.1021/jo8002612
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A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds
Yun-Yun Yang, Wang-Ge Shou, Zheng-Bo Chen, Deng Hong, and Yan-Guang Wang
pp 3928 - 3930; (Note) DOI: 10.1021/jo8003259
Abstract   Full:  HTML /  PDF (287K)  Supporting Info 
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Cation-Induced π-Stacking
Eric Bosch, Charles L. Barnes, Nathan L. Brennan, Galen L. Eakins, and Bryan E. Breyfogle
pp 3931 - 3934; (Note) DOI: 10.1021/jo800343f
Abstract   Full:  HTML /  PDF (467K)  Supporting Info 
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Organocatalytic and Enantioselective Synthesis of β-(Hydroxyalkyl)-γ-Butyrolactones
Saumen Hajra and Aswini Kumar Giri
pp 3935 - 3937; (Note) DOI: 10.1021/jo8005733
Abstract   Full:  HTML /  PDF (158K)  Supporting Info 
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Scalable Preparation of Both Enantiomers of 2-(1-Hydroxy-2-oxocyclohexyl)acetic Acid
Mitchell Vamos and Yoshihisa Kobayashi
pp 3938 - 3941; (Note) DOI: 10.1021/jo8000904
Abstract   Full:  HTML /  PDF (269K)  Supporting Info 
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Efficient Synthesis of Trifluoromethyl and Related Trisubstituted Alkene Dipeptide Isosteres by Palladium-Catalyzed Carbonylation of Amino Acid Derived Allylic Carbonates
Eriko Inokuchi, Tetsuo Narumi, Ayumu Niida, Kazuya Kobayashi, Kenji Tomita, Shinya Oishi, Hiroaki Ohno, and Nobutaka Fujii
pp 3942 - 3945; (Note) DOI: 10.1021/jo702318d
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Benzyl 2-Cyano-3,3-Dimethyl-1-pyrrolidinecarboxylate, a Versatile Intermediate for the Synthesis of 3,3-Dimethylproline Derivatives
Jesus R. Medina, Charles W. Blackledge, Karl F. Erhard, Jeffrey M. Axten, and William H. Miller
pp 3946 - 3949; (Note) DOI: 10.1021/jo7027163
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An Expedient Synthesis of Mellitic Triimides
Kathryn G. Rose, Dina A. Jaber, Chenaimwoyo A. Gondo, and Darren G. Hamilton
pp 3950 - 3953; (Note) DOI: 10.1021/jo800185v
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Room-Temperature Kumada Cross-Coupling of Unactivated Aryl Chlorides Catalyzed by N-Heterocylic Carbene-Based Nickel(II) Complexes
Zhenxing Xi, Bin Liu, and Wanzhi Chen
pp 3954 - 3957; (Note) DOI: 10.1021/jo800197u
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Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols
Xiaobo Zhou, Huimin Zhang, Xin Xie, and Yanzhong Li
pp 3958 - 3960; (Note) DOI: 10.1021/jo800232p
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