ORGNTuesday, March 25, 2003

8:00 PM-10:00 PM Convention Center -- Hall G,Poster
Methodology, Synthesis, Asymmetric Reactions, Process R&D
Poster Session
Organizer:L. McElwee-White
331A novel anionic anolog of the thia Fries rearrangement
Alan M. Dyke, Guy C. Lloyd-Jones, J. P. H. Charmant, Jeremy N. Harvey
332Desulfonylation of p-deficient heterocyclic sulfones
Pedro I Garcia Jr., Zhinzong Wang, Leigh N. Crain, Stanislaw F. Wnuk
333Lithiation of N-methyldiethanolamine-protected arylboronic acids: Preparation of novel arylboronic acids bearing sulfonylchloride/sulfonamide substituents
Per Vedso, Thomas Hoeg-Jensen, Preben H. Olesen
334Mono-deprotection of di-tert-butyl silylene ethers: A new protocol for selective protection of secondary alcohols
Brian L. Pagenkopf, Ming Yu
335Phosphadioxirane: A new reagent for nonradical epoxidation of alkenes
Jeff Joseph A. Celaje, Shabana Afzal, David Ho, Matthias Selke, Roumei Gao, Ha-Yong Chung
336Synthesis and structure determination of atropoisomeric ketimines
Said Gmouh, Jamal Jamal Eddine, Jacque F. Maddaluno, Hassan Oulyadi, Jean-Yves Valnot
337Synthesis of targretin using a chemoselective metal-catalyzed cross-coupling reaction of 1-iodo-1-tributylstannyl ethene
Miguel J. Dabdoub, Vania B. Dabdoub, Joseph P. Marino, Gabriela R. Hurtado
338Synthesis of temarotene and arotinoid using the metal-catalyzed cross-coupling reaction of vinyltellurium intermediates
Miguel J. Dabdoub, Vania B. Dabdoub, Joseph P. Marino
339Two approaches toward the total synthesis of (+)-pisatin
Maurice Marsini, Kristen Hyland, Eduard Casillas
340A combined metalation-cross-coupling strategy toward the synthesis of cervinomycin
Bert Nolte, Christian Hartung, Victor Snieckus
341Practical synthesis of a-aminoalkyl-a'-chloromethylketone derivatives via chloromethylation of N-benzylidene-protected amino acid esters
Tomoyuki Onishi, Yasuyuki Otake, Shinji Kuroda, Naoko Hirose, Kunisuke Izawa
342Catalytic C-C bond formation under hydrogenative conditions: Diastereoselective formation of quaternary centers via Rh-catalyzed aldol cycloreduction of mono-enone monoketones using elemental hydrogen as terminal reductant
Ryan R. Huddleston, Michael J. Krische
343Reductive generation of enolates from enones using elemental hydrogen: Catalytic C-C bond formation under hydrogenative conditions
Hye-Young Jang, Ryan R. Huddleston, Michael J Krische
344Eliminating aqueous workup in multiple-step solution-phase synthesis by flash chromatography
Shahnaz Ghassemi, Jack Liu, Peter Rahn
345Stereo- and regioselective synthesis of 1,3-diaryl-3-chloro-1-propanols
George W Kabalka, Yuhong Ju, Zhongzhi Wu
346Studies toward the synthesis of streptovaricin D
José A. Prieto, Wildeliz Torres
347Synthesis and reactivities of allenamides and ynamides
Michael R. Tracey, Richard P. Hsung, Jason A. Mulder, Hui Xiong, Rameshkumar Chellappan, Craig R. Berry, Mike O. Frederick
348Synthesis of 5-hydroxycyclopentenones via titanium intermediates
Anne M. Wilson, Robert A. Arbuckle
349Synthesis of biaryl a-ketophosphonic acids by aqueous Suzuki coupling reaction
Xianfeng Li, Liang Wang, Ashok Bhandari, Christopher P. Holmes, Anna K. Szardenings
350Synthesis of cyclooctenes
Mona Aasmul, Mukund P. Sibi
351Synthesis of dibenzo-14-crown-4 ethers bearing fluorinated alcohol sidearms
Frederick V. Sloop Jr., Peter V. Bonnesen
352Synthesis of lactams and other nitrogen heterocylces by intramolecular cyclizations of N-acyl derivatives of aminosulfones
Aravamudan S. Gopalan, Nora M. Hernandez, Melina J. Sedano, Hollie K. Jacobs
353Terminally functionalized polyisobutylene oligomers as supports for ligands and catalysts
Jun Li, David E. Bergbreiter
354The aqueous Prins reaction
Danielle L. Aubele, Paul E Floreancig
355The first copper-catalyzed amidation of haloalkynes and subsequent Marbet-Saucy rearrangements toward the synthesis of chiral allenes
Mike O. Frederick, Jason A. Mulder, Richard P. Hsung
356Silyl-substituted amino acid derivatives: Developing rapid routes to lactam-based peptide mimetic scaffolds
Haizhou Sun, Kevin D. Moeller
357Preparation of substituted allyl acetates and sulfonates from acetates of Baylis-Hillman adducts in ionic liquids
George W Kabalka, Bollu Venkataiah, Gang Dong
358Role of quaternary ammonium salts in oxidative reactions
Christopher T. Lloyd, James H. Wynne, Robert F. Cozzens, George W. Mushrush
359New methodology for the preparation of 3-hydroxy-2-pyridinone (3,2-HOPO) chelators. 2. Reaction of alcohols, thiols, phenols, and thiophenols with an electrophilic 3,2-HOPO precursor
Aravamudan S. Gopalan, Sumathi Chittamuru, Timothy N. Lambert, Gloria Martinez, Hollie K. Jacobs
360General approach for the synthesis of primary, secondary, and tertiary b-phenethylamines by reductive amination
Bruhaspathy Miriyala, Sukanta Bhattacharyya, John S. Williamson
361Investigation of 2-isoxazoline synthesis: A unique twist on the Mitsunobu reaction
Genessa M. Wood, Cindy C. Browder
362N-Alkenyl lactams derived from ketones
JiYoung Mun, Michael B. Smith
363Epoxidation of D5-steroids by dioxiranes generated in situ
Edward J. Parish, Zhihai Qiu
364Esters of 2-iodoxybenzoic acid: Novel periodinanes and oxidizing reagents
Viktor V. Zhdankin, Dmitry N. Litvinov, Alexey Y. Koposov, Rik R. Tykwinski, Brian P. Rempel
365Facile single-pot preparation of S-alkylthiocarbamates
James H. Wynne, Arthur W. Snow
366Further applications of N-heterocyclic carbenes as transesterification catalysts
Rohit Singh, Gabriela A. Grasa, S.P. Nolan
367Development of an efficient route to pentasubstituted acylferrocenes
Jakob Norinder, Hanna K. Cotton, Jan-E. Bäckvall
368Development of an organocatalytic intramolecular cyclopropanation reaction
Nadine Bremeyer, Matthew J. Gaunt, Steven V. Ley
369Direct conversion of amidoximes to amidines via transfer hydrogenation
Chad E. Stephens, Mariappan Anbazhagan, David W. Boykin
370Development of b-keto 1,3-dithianes: Versatile platforms for organic synthesis
Helen F. Sneddon, Matthew J. Gaunt, Steven V. Ley
371Conversion of epoxides to 1,3-dioxolanes catalyzed by tin(II) chloride
James R. Vyvyan, Jennifer A. Meyer, Korin D. Meyer
372Copper(I)-catalyzed synthesis of unsymmetrical triphenylphosphines
Derek Van Allen, D. Venkataraman
373CsOH-promoted P-alkylation: A convenient and highly efficient synthesis of tertiary phosphines and their metal complexes
Matthew T. Honaker, Benjamin J. Sandefur, Alicia L. McDaniel, Lester L. Pesterfield, Ralph Nicholas Salvatore
374Cyclooctanoid ring systems from mixed thioacetals via sulfur-assisted [1,2] shift of oxonium ylides
Fredrik P. Marmsater, Graham K. Murphy, F. G. West
375Deoxygenative alkylations of silyl ether derivatives of benzylic alcohols catalyzed by InCl3
Andrea S. Dupre, Martha Sibrian-Vazquez, David A Spivak
376An unexpected hydroxylation observed in selenoxide elimination reactions producing 4-hydroxy-conjugated carbonyl compounds
JiYoung Mun, Michael B. Smith
377Acylation and reductive amination of indole
Samuel D. Jensen, Wayne M. Stalick, James H. Wynne, Christopher T. Lloyd
378Aldol reactions of propionanilide dianions
David E. Lewis, Glen C. Gullickson, Russell G Baughman, Mushtaq A. Khan
379Amino acid-derived iodobenzene dicarboxylates: Reagents for oxidative conversion of alkenes to amino acid esters
Viktor V. Zhdankin, Vyacheslav V. Boyarskikh, Alexey E. Koposov, Brian Netzel
380A polymer-supported hydrophosphinylation catalyst
Sylvine Deprele, Jean-Luc Montchamp
381"Nonet-bracketing" in the 1H NMR spectrum: Quantification of low levels of water and other solutes in organic solutions
Thomas R. Hoye, Hollie J. Lewis, Seif-Eldin N. Ayyad
382(Z)-a-Haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates
D. K. Barma, Abhijit Kundu, Hongming Zhang, J. R. Falck
383Bismuth nitrate catalyzed Michael reactions of amines, imidazoles, thiols, and carbamates
Bimal K. Banik, Neeta Srivastava
384Bismuth nitrate catalyzed Michael reaction of indoles
Bimal K. Banik, Neeta Srivastava
385Cycloaddition of naphthalenyl and anthracenyl imines: Interesting aspects of the Staundinger reaction toward b-lactams
Bimal K. Banik, Indrani Banik, Linda Hackfeld
386Facile synthesis of heterocycles by indium-induced reduction-rearrangement of the nitro b-lactams
Bimal K. Banik, Indrani Banik, Mary Wilson
387Highly diastereoselective synthesis of 2,5-disubstituted-1,3-dioxolan-4-ones via molecular iodine-catalyzed reaction
Bimal K. Banik, Swapan K. Dasgupta
388Intramolecular coupling of diimines using a samarium-induced reaction: Synthesis of heterocycles
Bimal K. Banik, Swapan K. Dasgupta, Neeta Srivastava, Susanta Samajdar
389Remarkable new entry to N-unsubstituted b-lactams through a solid-phase approach
Bimal K. Banik, Swapan K. Dasgupta
390New bismuth nitrate induced stereospecific glycosylation of alcohols
Bimal K. Banik, Neeta Srivastava
391Oxidation of aromatic triisopropylsilylsulfanyls to sulfonyl chlorides: Preparation of sulfonide amides
Yves Gareau, Jonathan Pellicelli, Danny Gauvreau, Sébastien Laliberté
392Polymer-bound borohydrides: Selectivity and loading studies
James R. Blanton
393Investigating the diastereoselective cyclization of bissulfonyl esters
John Colucci
394Paper Withdrawn
395Cascade radical cyclizations of benzannulated enyne-allenes: Unusual cleavage of a benzene ring leading to twisted 1,1'-dialkyl-9,9'-bifluorenylidenes and spiro[1H-cyclobut[a]indene-1,9'-[9H]fluorenes]
Yonghong Yang, Jeffrey L. Petersen, Kung K. Wang
396Radical cyclizations of biradicals from thermolysis of [2-(1-alkynyl)phenyl]-N-phenylketenimines
Xiaoling Lu, Jeffrey L. Petersen, Kung K. Wang
397Selective deactivation of a single nitrogen of symmetrical diamines via complexation: Application to the monoacylation of symmetrical diamines
Zhongxing Zhang, Zhiwei Yin, Nicholas A. Meanwell, John F. Kadow, Tao Wang
398Synthesis of 2-aryl-benzo[b]furans via copper(I)-catalyzed coupling reaction of o-iodophenols and aryl acetylenes
Craig G. Bates, Pranorm Saejueng, Jaclyn Murphy, D. Venkataraman
399b-cyclodextrin-controlled Reimer-Tiemann reaction for N,N-dimethylaniline
Jigang Pan, Yuejun Huang
400Fluorous approach to synthesis and separation: Fluorous, chromatography-free Mitsunobu reaction
Roman Dembinski, Marcin W. Markowicz
401Practical ligands for copper-catalyzed ether-forming reactions
David Mitchell, Y. John Pu, Thomas M Koenig, Zhonghui Wan
402Efficient synthesis of 1,4-diaminophthalazines: An important moiety of E8010, a novel PDE type 5 inhibitor
Kazuhiro Yoshizawa, Shinya Abe, Yuki Komatsu, Ken Furukawa, Naoyuki Shimomura
403Study of the Corey-Kim intermediate by FT-IR
Gilles Chambournier, Herman Surjono, Zhenglong Xiao, Marius Naris
404Dynamic and classical resolution of aminobenzoazepinone
David Mitchell, Thomas M Koenig, Lynne A Hay, James E Audia, Stacey McDaniel, Jeffrey S Nissen
405Asymmetric synthesis of a potent AMPA potentiator
James A. Aikins, David Mitchell, Josh Davison, Dennis M. Zimmerman
406Improved synthesis of 3,3-dimethyl-4-piperidone
John R. Rizzo, Tony Y Zhang, Michael Staszak
407Enantioselective synthesis of (+)-kelsoene
Liming Zhang Sr., M. Koreeda
408Progress toward the total synthesis of peloruside A
Tiffany N. Heady, Michael T. Crimmins
409Studies toward the total synthesis of sclerophytin A utilizing a [4+3] annulation
Gary A. Molander, David J. St. Jean Jr., Julia Haas
410Studies toward the total synthesis of 10-hydroxyasimicin
Steven V. Ley, Darren J. Dixon, Gillian L. Nattrass, Elena Diez-Martin
411Studies toward the total synthesis of tagetitoxin
Michael J. Porter, Fabienne Saez
412The enantiospecific, stereospecific total synthesis of alstonisine and approach to the total synthesis of Nb-demethylalstophylline oxindole
Xiangyu Z. Wearing, James M. Cook
413Total synthesis of (-)-dihydroguaiaretic acid
R. Elizabeth Brewster, Suzanne B. Shuker
414Total synthesis of alliacol A via oxidative cyclization reactions
John M Mihelcic, Kevin D. Moeller
415Studies toward the total synthesis of anticancer marine natural product apratoxin A
Zheng-Shuang Xu, Zhi-Yong Chen, Tao Ye
416Studies toward the total synthesis of dolabriferol
Jonathan M. Goodman, Edward F. Makiyi, Alastair D.G. Donald
417Synthesis of heliannuol C and E via aromatic Claisen rearrangement
James R. Vyvyan, Jennifer A. Drew, Jennifer M. Oaksmith, Elaine M. Peterson, Bevin W. Parks
418Studies toward a total synthesis of bengazole A utilizing BDA-protected building blocks
Emily P. Balskus, Paul E. Brennan, Steven V. Ley
419Toward a total synthesis of thapsigargin
Steven V. Ley, Steven F. Oliver, Klemens Hogenauer, Oliver Simic
420Studies toward a total synthesis of Palau’amine: Construction of the DEF rings
Hongwang Du, Carl J. Lovely
421Progress toward the total synthesis of salvinorin A: A potent, non-nitrogenous k-opioid receptor selective agonist
Suryanarayana Vangapandu, Ashok Phillip, Jeremy D. Stewart, Jordan Zjawiony, Mitchell A. Avery, Christopher R. McCurdy
422Progress toward the total synthesis of brasilicardin A
Michael G. Lansdown, M. E. Jung
423A convergent approach to geranylated intermediates for synthesis of schweinfurthin B
Jeffrey D Neighbors, David F. Wiemer
424Efficient assembly of the oxazole subunit of leucascandrolide A
Jelena Janjic, Sergey A. Kozmin
425Efforts toward the total synthesis of debrominated flustramine C via asymmetric sulfur ylide rearrangements
Amir Sabahi, Jon D. Rainier
426Progress toward the synthesis of Fistulina hepatica natural products
David M. Schwope, Gordon V. Givan, Robert E. Minto
427Studies directed toward the synthesis of the decahydroquinoline 275B series
Edith J. Banner, Mark L. Trudell
428Approaches to the total synthesis of stemona alkaloids
Thangaiah Subramanian, Mukund P. Sibi
429Progress toward the synthesis of an anti-inflammatory acetophenone glucoside
Matthew R. Dintzner, Kristen M. McClelland, Debbie Coligado
430Studies toward the total synthesis of (+)- isoschizandrin
Gary A. Molander, Kelly M. George, Lauren Gilchrist-Monovich
431Synthetic studies of (+)-himbacine and its congeners featuring an intermolecular Diels-Alder reaction
Masanori Takadoi, Tomoyuki Kawai, Kentaro Yamaguchi, Shiro Terashima
432Diels-Alder approach to cis-clerodane natural products: First total synthesis of solidago alcohol
Tai Wei Ly, Jyh-Hsiung Liao, Kak-Shan Shia, Hsing-Jang Liu
433Amine-catalyzed direct asymmetric Mannich-type reactions: Enantioselective synthesis of amino acid and amino alcohol derivatives
Armando Cordova
434Asymmetric synthesis of substituted cyclopentenone derivatives
Morgan Menard, Jeremy Robertson, Rhonan Ford
435Water-accelerated tandem catalytic carboalumination-Claisen rearrangements
David L. Waller, Peter Wipf, Jonathan T. Reeves
436Regioselective and diastereoselective allylic amination using chlorosulfonyl isocyanate: A novel asymmetric synthesis of unsaturated 1,2-amino alcohols
Young Hoon Jung, Ji Duck Kim, Insoo Kim, Ok Pyo Zee
437Stereospecific synthesis of trans-2,3-diaryl-substituted 1-aminocyclopropanecarboxylic acid derivatives(II)
Guifa Su, Ling Pan, Hongtao Mu, Longmei Zeng, Robert P. Hammer
438Syntheses of new chiral monodentate phosphite ligands and their use in asymmetric hydrogenations
Zihao Hua, Victor C. Vassar, Iwao Ojima
439Mechanistic studies of enantioselective conjugate radical additions
Jake Zimmerman, Shankar Manyem, Mukund P. Sibi
440Nonlinear effects operate when chiral BINOL-boron Lewis acids are used for asymmetric catalysis
Yolanda Pérez Fuertes, Susumu Arimori, Steven D. Bull, Jean Philippe Cros, Tony D. James
441Novel biocatalytic route to b,g-epoxy alcohols
Charles A. G. Baker-Glenn, Virginie Maggiotti, Rachael Ancliff, Véronique Gouverneur
442Intramolecular reactions of chiral allylsilanes with in situ-generated acyliminium ions
Weston R. Judd, Sooho Ban, Kristine E. Frank, Jeffrey Aubé
443Investigation of the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ
Nga-Wai Chung, Man-Kin Wong, Dan Yang
444Hemiacetal ester formation in lipase-catalyzed transesterifications of vinyl esters with hindered secondary alcohols
Dan Isaksson, Marica L. Henriksson, Kristina Sjödin, Hans-Erik Högberg
445Highly diastereoselective aldol addition reactions of N3-substituted 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones
Shawn R. Hitchcock, Trisha R. Hoover
446Highly enantioselective sulfur ylide epoxidation reactions
Jonathan M. Goodman, Benjamin R. Bellenie
447Development of nucleophilic chiral pyridine catalysts: Applications in asymmetric quaternary carbon synthesis
Edwin Vedejs, Scott A. Shaw
448Diastereoselective conjugate addition of Grignard reagents to fumaramides derived from Oppolzer's sultam
Gary P. Reid, David J. Robins
449Asymmetric synthesis of all diastereomers of (2,3,4)-3-hydroxy-2,4,6-trimethylheptanoic acid: Verification of configurational assignment
Jeffrey A. Turk, Mark A. Lipton
450Conformational analysis and asymmetric application of a structurally novel chiral auxiliary: Progress toward the synthesis of saquinavir
Shawn R. Hitchcock, James R. Burgeson
451Asymmetric catalyzed reactions using recoverable catalysts
Richard J Eaves, Martin Wills, Osamu Ichihara
452Asymmetric approach to proline-derived spiro-b-lactams: Staudinger reaction of N-protected trans-4-methylsulfonyloxy-L-proline with N-aryl imines
Alisher B. Khasanov, Michele M. Ramirez-Weinhouse, Thomas R. Webb, Mohan Thiruvazhi
453A new strategy for the use of chiral auxiliaries in asymmetric synthesis
Frederic J. Feuillet, Steven D. Bull
454Amination of activated hydrocarbons using chloramine-T and copper catalysts: Applications to enantioselective synthesis
Christopher M. Parsons, Paul C. Taylor, Jacob L. Irwin, D. James Wilson, Shaun M. Fillery
455Novel stereoselective route to benzindene prostacyclins: The large-scale synthesis of RemodulinTM (treprostinil, UT-15)
James P. Staszewski, Robert M. Moriarty, Liang Guo, Raju Penmasta, Neena Rani, Sudersan M. Tuladhar, David Crich, Livia A. Enache, Om Prakash
456Heterogeneous asymmetric transfer hydrogenation using norephedrine ruthenium complexes adsorbed on mesoporous silica
Woo Sung Kim, Hong Myung Lee, Sang-Wook Kim, Jinwoo Lee, Taeghwan Hyeon, B. Moon Kim
457Non-C2-symmetric ligands for asymmetric catalysis
Ruzhou Zhang, Mukund P. Sibi
458A new efficient bisdinaphthophosphepine ligand for asymmetric hydrogenation
Wenjun Tang, Xumu Zhang
459Recovery and reuse of a soluble polymer-supported asymmetric catalyst for the addition of diethylzinc to aldehydes
Uche K. Anyanwu, Dhandapani Venkataraman
460Highly enantioselective alkenylation of aldehydes promoted by chiral tertiary aminonaphthol
Jian-Xin Ji, C. W. Yip, Albert S. C. Chan
461Asymmetric conjugate addition reactions of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine, (1S,2S)-pseudoephedrine, and (1R,2S)-norephedrine: Progress toward the asymmetric synthesis of (+)-tolterodine
Shawn R. Hitchcock, Jennifer R. Blackburn

Symposium Grid -- Division of Organic Chemistry -- Session Listing

The 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003