Organic Syntheses, Volume 87

by Ellman, Jonathan A.

• ISBN13: 9781118005149
• ISBN10: 1118005147
• Edition: 1st
• Format: Hardcover
• Copyright: 2011-01-04
• Publisher: Wiley
• More Book Details

Summary

Organic syntheses consists of protocols for the synthesis of useful chemical compounds. Organic Syntheses, Volume 87 provides carefully checked and edited experimental protocols that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. For each protocol, safety warnings are presented along with detailed experimental descriptions for the preparation, purification, and identification of the compound. Additionally, special reaction conditions are also detailed. This current volume continues the tradition of providing significant and interesting procedures for synthetic chemists working in increasingly diverse areas.

Author Biography

Peter Wipf is the Director of the Combinatorial Chemistry Center (CCC) and the Center for Chemical Methodologies and Library Development (UPCMLD) which are involved in many collaborative projects in Chemical Biology. He is also a founding member of the Center for Medical Countermeasures Against Radiation (CMCR) and the University of Pittsburgh Center for Chemical Diversity (UPCDC). He has served on the organizing committee of several conferences and workshops, including the NSF Workshop on Organic Synthesis. He is a member of several editorial boards, including Medicinal Chemistry Letters (ACS MCL), Organic Reactions (OR), and Organic Syntheses (OS).

Table of Contents

Metal-Free One-Pot Oxidative Amination of Aromatic Aldehydes: Conversion of Benzaldehyde to N-Benzoyl Pyrrolidine 1
Kekeli Ekoue-Kovi and Christian Wolf

A Practical and Scalable Synthesis of N-Halo Compounds: 2-Chloro-6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline 8
Yong-Li Zhong and Paul G. Bulger

Regioselective C-4 Bromination of Oxazoles: 4-Bromo-5-(Thiophen-2-YL) Oxazole 16
Bryan Li, Richard A. Buzon, and Zhijun Zhang

Synthesis of Spiroborate Esters from 1,2-Aminoalcohols, Ethylene Glycol and Triisopropyl Borate: Preparation of (S)-1-(1,3,2-Dioxaborolan-2-Yloxy)-3-Methyl-1,1-Diphenylbutan-2-Amine 26
Viatcheslav Stepanenko, Kun Huang and Margarita Ortiz-Marciales

Catalytic Enantioselective Borane Reduction of Benzyl Oximes: Preparation of (S)-1-Pyridin-3-YL-Ethylamine BIS Hydrochloride 36
Kun Huang and Margarita Ortiz-Marciales

Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation 53
Naohiro Kirai and Yoshihiko Yamamoto

Preparation of (S)-3,3’-BIS-Morpholinomethyl-5,5’,6,6’,7,7’,8,8’-Octahydro-1,1’-BI-2-Naphthol 59
Mark Turlington and Lin Pu

Catalytic Asymmetric Addition of an In-Situ Prepared Arylzinc to Cyclohexanecarboxaldehyde: (R)-(+)-α-Cyclohexyl-3-Methoxy-Benzenemethanol 68
Albert M. DeBerardinis, Mark Turlington, and Lin Pu

Microwave-Assisted Synthesis of 1,3-Dimesitylimidazolinium Chloride 77
Morgan Hans and Lionel Delaude

Synthesis of (3-Chlorobutyl)Benzene by the Cobalt-Catalyzed Hydrochlorination of 4-Phenyl-1-Butene 88
Boris Gaspar, Jerome Waser, and Erick M. Carreira

Synthesis of Substituted Indazoles via (3+2) Cycloaddition of Benzyne and Diazo Compounds 95
Feng Shi and Richard C. Larock

Palladium-Catalyzed Cross-Coupling Using an Air-Stable Trimethylaluminum Source. Preparation of Ethyl 4-Methylbenzoate 104
Andrej Vinogradov and Simon Woodward

Synthesis of Dimethyl 2-Phenycyclopropane-1,1-Dicarboxylate Using an Iodonium Ylide Derived from Dimethyl Malonate 115
Sébastien R. Goudreau, David Marcoux and Andre B. Charette

New, Convenient Route for Trifluoromethylation of Steroidal Molecules 126
Xiang-Shu Fei, Wei-Sheng Tian, Kai Ding, Yun Wang and Qing-Yun Chen

Preparation of Ethyl 1-Benzyl-4-Fluoropiperidine-4-Carboxylate 137
Jianshe Kong, Tao Meng, Pauline Ting, and Jesse Wong

Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to α,ß-Unsaturated Esters: Asymmetric Synthesis of (S)-ß-Leucine 143
Stephen G. Davies, Ai M. Fletcher, and Paul M. Roberts

Cyclohexene Imine (7-Aza-Bicyclo[4.1.0]Heptane) 161
Iain D. G. Watson, Nicholas Afagh and Andrei K. Yudin

Preparation of (E)-(2-Iodovinyl)Benzene From Benzyl Bromide and Diiodomethane 170
James A. Bull, James J. Mousseau and André B. Charette

Synthesis of Tetraorganosilanes: (Chloromethyl)Dimethylphenylsilane 178
Submitted by Kei Murakami, Hideki Yorimitsu, and Koichiro Oshima

A General Method for Copper-Catalyzed Arylation of Acidic Arene C-H Bonds. Preparation of 2-Chloro-5-(3-Methylphenyl)-Thiophene 184
Joseph Alvarado, Hien-Quang Do, and Olafs Daugulis

1,3,5-Triacetylbenzene 192
Peter J. Alaimo, Amanda-Lynn Marshall, David M. Andrews and Joseph M. Langenhan

Organocatalytic α-Methylenation of Aldehydes: Preparation of 3,7-Dimethyl-2-Methylene-6-Octenal 201
Meryem Benohoud, Anniina Erkkilä, and Petri M. Pihko

Ruthenium-Catalyzed Arylation of Ortho C-H Bond in an Aromatic with an Arylboronate: 8-Phenyl-1-Tetralone 209
Kentaroh Kitazawa, Takuya Kochi, and Fumitoshi Kakiuchi

Amide Formation by Decarboxylative Condensation of Hydroxylamines and α-Ketoacids: N-[(1S)-1 Phenylethyl]-Benzeneacetamide 218
Lei Ju and Jeffrey W. Bode

One-Pot Diazotization and Heck Reaction of Methyl Anthranilate: 2-(3-Oxopropyl) Benzoic Acid Methyl Ester 226
Florencio Zaragoza

Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-Alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-Phenylethynyl)-N-(Phenylmethyl)Benzenesulfonamide 231
Alexis Coste, François Couty and Gwilherm Evano

Direct Fluorination of the Carbonyl Group of Benzophenones Using Deoxo-Fluor®: Preparation of BIS(4-Fluorophenyl) Difluoromethane 245
Ying Chang, Hyelee Lee, Chulsung Bae

Preparation and [2+2] Cycloaddition of 1-Triisopropylsiloxy-1-Hexyne with Methyl Crotonate: 3-Butyl-4-Methyl-2-Triisopropylsiloxy-Cyclobut-2-Enecarboxylic Acid Methyl Ester 253
Valeriy Shubinets, Michael P. Schramm, and Sergey A. Kozmin

Pd(0)-Catalyzed Asymmetric Allylic and Homoallylic Diamination of 4-Phenyl-1-Butene with DI-Tert-Butyldiaziridinone 263
Baoguo Zhao, Haifeng Du, Renzhong Fu, and Yian Shi

Synthesis of Enamides from Ketones: Preparation of N-(3,4-Dihydronaphthalene-1-YL)Acetamide 275
Hang Zhao, Charles P. Vandenbossche, Stefan G. Koenig, Surendra P. Singh, and Roger P. Bakale

Safe and Scalable Preparation of Barluenga’s Reagent 288
Justin M. Chalker, Amber L. Thompson, and Benjamin G. Davis

Palladium-Catalyzed Alkyl-Alkyl Suzuki Cross-Couplings of Primary Alkyl Bromides at Room Temperature: (13-Chlorotridecyloxy)Triethylsilane 299
Sha Lou and Gregory C. Fu

Synthesis of Chiral Pyridine Bis(Oxazoline) Ligands for Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary allylic Chlorides with Alkylzincs:2,6-BIS[(4R)-4,5-Dihydro-4-(2-Phenylethyl)-2-Oxazolyl]-Pyridine 310
Sha Lou and Gregory C. Fu

Nickel-Catalyzed Asymetric Negishi Cross-Couplings of Racemic Secondary Allylic Chlorides with Alkylzincs: (S,E)-Ethyl 6-(1,3-Dioxolan-2-YL)-4-Methylhex-2-Enoate 317
Sha Lou and Gregory C. Fu

Nickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary a-Bromo Amides with Alkylzinc Reagents: (s)-N-Benzyl-7-Cyano-2-Ethyl-N-Phenylheptanamide 330
Sha Lou and Gregory C. Fu

One-Pot Synthesis of 5H-Indazolo-[3,2-b] Benzo[d]-1,3-Oxazine: Two Efficient Preparative Methods 339
Danielle M. Solano, Jeffrey D. Butler, Makhluf J. Haddadin and Mark J. Kurth

Preparation of Chiral and Achiral Triazolium Salts: Carbene Precursors with Demonstrated Synthesis Utility 350
Harit U. Vora, Stephen P. Lathrop, Nathan T. Reynolds, Mark S. kerr, Javier Read de Alaniz, and Tomislav Rovis

Synthesis of A N-Mesityl Substituted Aminoindanol-Derived Triazolium Salt 362
Justin R. Struble and Jeffrey W. Bode

Preparation of O-Allyl-N-(9-Anthracenyl-Methyl)-Cinchonidium Bromide as a Phase Transfer Catalyst 377
E. J. Corey and Mark C. Noe