Table of Contents

April 29, 2005
Volume 70, Issue 9
Pages 3343-3764

About the Cover: The oxidation of an alcohol to the corresponding carbonyl product using a Pd-catalyst, an air atmosphere as the source of molecular oxygen, and the stoichoimetric reoxidant shown in the flask is depicted. See Sigman and co-workers, p 3343. View the article.

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Articles

Development and Comparison of the Substrate Scope of Pd-Catalysts for the Aerobic Oxidation of Alcohols

Mitchell J. Schultz, Steven S. Hamilton, David R. Jensen, and Matthew S. Sigman
pp 3343–3352
Publication Date (Web): December 30, 2004 (Article)
DOI: 10.1021/jo0482211

Synthesis of 2,2-Disubstituted Pyrrolidine-4-carboxylic Acid Derivatives and Their Incorporation into β-Peptide Oligomers

Bayard R. Huck and Samuel H. Gellman
pp 3353–3362
Publication Date (Web): April 05, 2005 (Article)
DOI: 10.1021/jo048639z

Palladium-Diphosphite Catalysts for the Asymmetric Allylic Substitution Reactions

Montserrat Diéguez, Oscar Pàmies, and Carmen Claver
pp 3363–3368
Publication Date (Web): March 24, 2005 (Article)
DOI: 10.1021/jo0480904

Diastereoselective Ring Expansion of β-Lactams toward γ-Lactams via N-Acyliminium Intermediates

Willem Van Brabandt and Norbert De Kimpe
pp 3369–3374
Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jo048158f

Reaction of Metalated Nitriles with Enones

Hans J. Reich, Margaret M. Biddle, and Robert J. Edmonston
pp 3375–3382
Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jo0478050

Synthesis of Selected LeY and KH-1 Analogues:  A Medicinal Chemistry Approach to Vaccine Optimization

Maria K. Spassova, William G. Bornmann, Govindaswami Ragupathi, George Sukenick, Philip O. Livingston, and Samuel J. Danishefsky
pp 3383–3395
Publication Date (Web): April 05, 2005 (Article)
DOI: 10.1021/jo048016l

Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s

Huahua Jian and James M. Tour
pp 3396–3424
Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jo048051s

Reaction of 2-Methoxy-3H-azepine with NBS:  Efficient Synthesis of 2-Substituted 2H-Azepines

Christopher E. J. Cordonier, Kyosuke Satake, Mikihiko Atarashi, Yousuke Kawamoto, Hideki Okamoto, and Masaru Kimura
pp 3425–3436
Publication Date (Web): March 15, 2005 (Article)
DOI: 10.1021/jo0500232

Experimental and Theoretical Study of Stabilization of Delocalized Forms of Semibullvalenes and Barbaralanes by Dipolar and Polarizable Solvents. Observation of a Delocalized Structure that Is Lower in Free Energy than the Localized Form

Maximilian Seefelder, Markus Heubes, Helmut Quast, W. Daniel Edwards, John R. Armantrout, Richard Vaughan Williams, Christopher J. Cramer, Alan C. Goren, David A. Hrovat, and Weston Thatcher Borden
pp 3437–3449
Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jo0502089

Conformational Mobility of Thianthrene-5-oxide

María Elena González-Núñez, Rossella Mello, Jorge Royo, Gregorio Asensio, Isidro Monzó, Francisco Tomás, Jesús García López, and Fernando López Ortiz
pp 3450–3457
Publication Date (Web): April 06, 2005 (Article)
DOI: 10.1021/jo048802q

Photochemistry of Substituted Dibenzothiophene Oxides: The Effect of Trapping Groups1

Mrinmoy Nag and William S. Jenks
pp 3458–3463
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo047995e

Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents:  Synthesis of Optically Active Homoallylic Amines

Tirayut Vilaivan, Chutima Winotapan, Vorawit Banphavichit, Tetsuro Shinada, and Yasufumi Ohfune
pp 3464–3471
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo0477244

Antioxidant Properties of Natural and Synthetic Chromanol Derivatives:  Study by Fast Kinetics and Electron Spin Resonance Spectroscopy

Wolfgang Gregor, Gottfried Grabner, Christian Adelwöhrer, Thomas Rosenau, and Lars Gille
pp 3472–3483
Publication Date (Web): March 30, 2005 (Article)
DOI: 10.1021/jo047927s

Chemoenzymatic Taxanes Approach Using Both Enantiomers of the Same Building Block. 2. Taxol CD Ring Unit

Jean-Pierre Uttaro, Gérard Audran, and Honoré Monti
pp 3484–3489
Publication Date (Web): March 24, 2005 (Article)
DOI: 10.1021/jo050039s

Reactions of Indole Derivatives with Oxiranes and Aziridines on Silica. Synthesis of β-Carbolin-1-one Mimic of Pancratistatin

Tomas Hudlicky, Uwe Rinner, Kevin J. Finn, and Ion Ghiviriga
pp 3490–3499
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo040292c

Direct Synthesis of Palladium Porphyrins from Acyldipyrromethanes

Duddu S. Sharada, Ana Z. Muresan, Kannan Muthukumaran, and Jonathan S. Lindsey
pp 3500–3510
Publication Date (Web): March 31, 2005 (Article)
DOI: 10.1021/jo050120v

Synthesis of Polycyclic Aromatics and Heteroaromatics via Electrophilic Cyclization

Tuanli Yao, Marino A. Campo, and Richard C. Larock
pp 3511–3517
Publication Date (Web): March 23, 2005 (Article)
DOI: 10.1021/jo050104y

New Glycosidase Activated Nitric Oxide Donors:  Glycose and 3-Morphorlinosydnonimine Conjugates

T. Bill Cai, Dongning Lu, Xiaoping Tang, Yalong Zhang, Megan Landerholm, and Peng George Wang
pp 3518–3524
Publication Date (Web): March 23, 2005 (Article)
DOI: 10.1021/jo050010o

1,4-Difluoro-2,5-dimethoxybenzene as a Precursor for Iterative Double Benzyne−Furan Diels−Alder Reactions

Gillian E. Morton and Anthony G. M. Barrett
pp 3525–3529
Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jo050112e

Kinetics and Mechanism of the Pyridinolysis of S-2,4-Dinitrophenyl 4-Substituted Thiobenzoates

Enrique A. Castro, Raul Aguayo, Jorge Bessolo, and José G. Santos
pp 3530–3536
Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jo050119w

Synthesis, Structure, and Reactivity of Novel 3,4-Diphosphacyclobutenes Bearing Silyl Groups

Shigekazu Ito, Hiromichi Jin, Shigeo Kimura, and Masaaki Yoshifuji
pp 3537–3541
Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jo050195z

Multicomponent Synthesis of 2-Imidazolines

Robin S. Bon, Bart van Vliet, Nanda E. Sprenkels, Rob F. Schmitz, Frans J. J. de Kanter, Christian V. Stevens, Marcel Swart, F. Matthias Bickelhaupt, Marinus B. Groen, and Romano V. A. Orru
pp 3542–3553
Publication Date (Web): March 30, 2005 (Article)
DOI: 10.1021/jo050132g

Novel Vinyl Phosphonates and Vinyl Boronates by Halogenation, Allylation, and Propargylation of α-Boryl- and α-Phosphonozirconacyclopentenes

Shoshana Ben-Valid, Abed Al Aziz Quntar, and Morris Srebnik
pp 3554–3559
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo047913m

The Phane Properties of anti-[2.2](1,4)Biphenylenophane

Man-kit Leung, M. Balaji Viswanath, Pi-Tai Chou, Shih-Chieh Pu, Hsin-Chieh Lin, and Bih-Yaw Jin
pp 3560–3568
Publication Date (Web): April 06, 2005 (Article)
DOI: 10.1021/jo047802n

Efficient Access to 2-Aryl-3-Substituted Benzo[b]thiophenes

Emilie David, Julie Perrin, Stéphane Pellet-Rostaing, Jérémie Fournier dit Chabert, and Marc Lemaire
pp 3569–3573
Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jo0500378

Improving Glycopeptide Synthesis:  A Convenient Protocol for the Preparation of β-Glycosylamines and the Synthesis of Glycopeptides

Christian P. R. Hackenberger, Mary K. O'Reilly, and Barbara Imperiali
pp 3574–3578
Publication Date (Web): March 31, 2005 (Article)
DOI: 10.1021/jo047801v

Electrophilic Cleavage of Cyclopropylmethystannanes:  An Experimental Comparison of σ−σ and σ−π Conjugation

Andrew J. Lucke and David J. Young
pp 3579–3583
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo047822p

Transfer Hydrogenation of Activated CC Bonds Catalyzed by Ruthenium Amido Complexes:  Reaction Scope, Limitation, and Enantioselectivity

Dong Xue, Ying-Chun Chen, Xin Cui, Qi-Wei Wang, Jin Zhu, and Jin-Gen Deng
pp 3584–3591
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo0478205

Enantioselective Nitrile Anion Cyclization to Substituted Pyrrolidines. A Highly Efficient Synthesis of (3S,4R)-N-tert-Butyl-4-Arylpyrrolidine-3-Carboxylic Acid

John Y. L. Chung, Raymond Cvetovich, Joseph Amato, J. Christopher McWilliams, Robert Reamer, and Lisa DiMichele
pp 3592–3601
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo050178+

Computational Evaluation of the Evidence for Tri-trans-[12]Annulene

Claire Castro, William L. Karney, Catherine M. H. Vu, Stephen E. Burkhardt, and Miguel A. Valencia
pp 3602–3609
Publication Date (Web): March 31, 2005 (Article)
DOI: 10.1021/jo047955a

Theoretical Study on the Isomerization Behavior between α,β-Unsaturated Acyl Radicals and α-Ketenyl Radicals

Hiroshi Matsubara, Ilhyong Ryu, and Carl H. Schiesser
pp 3610–3617
Publication Date (Web): March 24, 2005 (Article)
DOI: 10.1021/jo047868i

Total Syntheses of Yingzhaosu A and of Its C(14)-Epimer Including the First Evaluation of Their Antimalarial and Cytotoxic Activities

Alex M. Szpilman, Edward E. Korshin, Haim Rozenberg, and Mario D. Bachi
pp 3618–3632
Publication Date (Web): March 24, 2005 (Article)
DOI: 10.1021/jo050074z

Substituent Effects on the Ring Opening of 2-Aziridinylmethyl Radicals

Yi-Min Wang, Yao Fu, Lei Liu, and Qing-Xiang Guo
pp 3633–3640
Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jo048068a

The Strength of Parallel-Displaced Arene−Arene Interactions in Chloroform

Benjamin W. Gung, Xiaowen Xue, and Hans J. Reich
pp 3641–3644
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo050049t

Star-Shaped and Linear Nanosized Molecules Functionalized with Hexa-peri-hexabenzocoronene:  Synthesis and Optical Properties

Xiao-Yu Cao, Hong Zi, Wei Zhang, Hua Lu, and Jian Pei
pp 3645–3653
Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jo0480139

Simple Diastereoselectivity of the BF3·OEt2-Catalyzed Vinylogous Mukaiyama Aldol Reaction of 2-(Trimethylsiloxy)furans with Aldehydes

Carlos Silva López, Rosana Álvarez, Belén Vaz, Olalla Nieto Faza, and Ángel R. de Lera
pp 3654–3659
Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jo0501339

Molecular Diversity via Amino Acid Derived α-Amino Nitriles:  Synthesis of Spirocyclic 2,6-Dioxopiperazine Derivatives

Juan A. González-Vera, M. Teresa García-López, and Rosario Herranz
pp 3660–3666
Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jo050146m

Novel Behavior of O-Methylated β-Cyclodextrins in Inclusion of meso-Tetraarylporphyrins

Koji Kano, Ryuhei Nishiyabu, and Ryoji Doi
pp 3667–3673
Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jo0500535

N-Alkenyl-2-aziridinylmethyl Radicals and N-Alkenylaminyl Radicals in Cascade Cyclizations to Pyrrolizidines and Indolizidines

V. Van Speybroeck, N. De Kimpe, and M. Waroquier
pp 3674–3681
Publication Date (Web): April 06, 2005 (Article)
DOI: 10.1021/jo050067a

AuBr3- and Cu(OTf)2-Catalyzed Intramolecular [4 + 2] Cycloaddition of Tethered Alkynyl and Alkenyl Enynones and Enynals:  A New Synthetic Method for Functionalized Polycyclic Hydrocarbons

Naoki Asao, Kenichiro Sato, Menggenbateer, and Yoshinori Yamamoto
pp 3682–3685
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo0500434

Synthesis of Photoactivatable Acyclic Analogues of the Lobatamides

Ruichao Shen, Takao Inoue, Michael Forgac, and John A. Porco, Jr.
pp 3686–3692
Publication Date (Web): April 02, 2005 (Article)
DOI: 10.1021/jo0477751

Intramolecular Interactions between Chalcogen Atoms:  Organoseleniums Derived from 1-Bromo-4-tert-butyl-2,6-di(formyl)benzene

Sanjio S. Zade, Snigdha Panda, Harkesh B. Singh, Raghavan B. Sunoj, and Ray J. Butcher
pp 3693–3704
Publication Date (Web): March 31, 2005 (Article)
DOI: 10.1021/jo0478656

Notes

Hammett Correlation of Nornicotine Analogues in the Aqueous Aldol Reaction:  Implications for Green Organocatalysis

Claude J. Rogers, Tobin J. Dickerson, Andrew P. Brogan, and Kim D. Janda
pp 3705–3708
Publication Date (Web): March 31, 2005 (Note)
DOI: 10.1021/jo050161r

A Three-Component Photoreversible Tag for Thiols

Kristine M. Clarke, James J. La Clair, and Michael D. Burkart
pp 3709–3711
Publication Date (Web): March 26, 2005 (Note)
DOI: 10.1021/jo0481396

Asymmetric Henry Reaction Catalyzed by C2-Symmetric Tridentate Bis(oxazoline) and Bis(thiazoline) Complexes:  Metal-Controlled Reversal of Enantioselectivity

Da-Ming Du, Shao-Feng Lu, Tao Fang, and Jiaxi Xu
pp 3712–3715
Publication Date (Web): March 26, 2005 (Note)
DOI: 10.1021/jo050097d

Light, Medium, and Heavy Fluorous Triarylphosphines Exhibit Comparable Reactivities to Triphenylphosphine in Typical Reactions of Triarylphosphines

Dennis P. Curran, Xiao Wang, and Qisheng Zhang
pp 3716–3719
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo050116j

Reversed Approach to S-Farnesylation and S-Palmitoylation:  Application to an Efficient Synthesis of the C-Terminus of Lipidated Human N-Ras Hexapeptide

Kandasamy Pachamuthu, Xiangming Zhu, and Richard R. Schmidt
pp 3720–3723
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo0482357

N6-Arylation of 2‘-Deoxyadenosine via Copper-Catalyzed Direct Coupling with Aryl Halides

Chongzhao Ran, Qing Dai, and Ronald G. Harvey
pp 3724–3726
Publication Date (Web): March 30, 2005 (Note)
DOI: 10.1021/jo040284w

A Rapid Synthesis of 2-Aryl-5-substituted-2,3-dihydrobenzofurans

Jeffrey T. Kuethe, Audrey Wong, Michel Journet, and Ian W. Davies
pp 3727–3729
Publication Date (Web): March 24, 2005 (Note)
DOI: 10.1021/jo0500941

Single and Double Suzuki−Miyaura Couplings with Symmetric Dihalobenzenes

David J. Sinclair and Michael S. Sherburn
pp 3730–3733
Publication Date (Web): March 24, 2005 (Note)
DOI: 10.1021/jo050105q

Copper-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Grignard Reagents

Wei Zhang, Li-Xin Wang, Wen-Jian Shi, and Qi-Lin Zhou
pp 3734–3736
Publication Date (Web): March 24, 2005 (Note)
DOI: 10.1021/jo050015l

Enzymatic Removal of Carboxyl Protecting Groups. 1. Cleavage of the tert-Butyl Moiety

Marlen Schmidt, Efrosini Barbayianni, Irene Fotakopoulou, Matthias Höhne, Violetta Constantinou-Kokotou, Uwe T. Bornscheuer, and George Kokotos
pp 3737–3740
Publication Date (Web): March 23, 2005 (Note)
DOI: 10.1021/jo050114z

A Tandem Heck-Carbocyclization/Suzuki-Coupling Approach to the Stereoselective Syntheses of Asymmetric 3,3-(Diarylmethylene)indolinones

Wing S. Cheung, Raymond J. Patch, and Mark R. Player
pp 3741–3744
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo050016d

Enantioselective Total Synthesis of (−)-Curcuquinone via Regioselective Chromium-Mediated Benzannulation

Ana Minatti and Karl Heinz Dötz
pp 3745–3748
Publication Date (Web): April 05, 2005 (Note)
DOI: 10.1021/jo0500939

Enantioselective Syntheses of (+)-Xylarenal A and ent-Xylarenal A

Sandra Díaz, Asensio González, Ben Bradshaw, Javier Cuesta, and Josep Bonjoch
pp 3749–3752
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo0502450

Sulfur-Based Protecting Groups for Pyrroles and the Facile Deprotection of 2-(2,4-Dinitrobenzene)sulfinyl and Sulfonyl Pyrroles

Alison Thompson, R. Jonathan Butler, Meaghan N. Grundy, Andrea B. E. Laltoo, Katherine N. Robertson, and T. Stanley Cameron
pp 3753–3756
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo050077b

A Catalytic Enantioselective Hetero Diels−Alder Approach to the C20−C32 Segment of the Phorboxazoles

Brian S. Lucas, Laura M. Luther, and Steven D. Burke
pp 3757–3760
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo050034v

Template Effect of Tetrathiafulvalene in the Formation of Cyclobis(paraquat-p-phenylene)

Giancarlo Doddi, Gianfranco Ercolani, Paolo Mencarelli, and Alessio Piermattei
pp 3761–3764
Publication Date (Web): April 02, 2005 (Note)
DOI: 10.1021/jo050263h
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