Publisher Description

The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.

Author Biography

Margaret M. Faul received her B.Sc. and M.Sc degrees from University College Dublin, Ireland. She then moved to the US where she received her Ph.D. degree in synthetic organic chemistry from Harvard University with Professor David A. Evans. In 1993 Margaret joined the Chemical Process group at Eli Lilly and Company, and in 2003 she moved to Amgen where she is currently the Executive Director in the Process Development organization. At Amgen, Margaret is responsible for the commercial process development and process characterization of all molecules in both the synthetic and biologic Amgen portfolio.

Table of Contents

Preparation of Aryl Alkyl Ketenes 1
Nicholas D. Staudaher, Joseph Lovelace, Michael P. Johnson, and Janis Louie Preparation of Diisopropylammonium Bis(catecholato)cyclohexylsilicate 16
Kingson Lin, Christopher B. Kelly, Matthieu Jouffroy, and Gary A.Molander Continuous Flow Hydration of Pyrazine-2-carbonitrile in a Manganese Dioxide Column Reactor 34
Claudio Battilocchio, Shing-Hing Lau, Joel M. Hawkins, and Steven V. Ley Site-Selective C-H Fluorination of Pyridines and Diazines with AgF2 46
Patrick S. Fier and John F. Hartwig Site-Selective C-H Fluorination of Pyridines and Diazines with AgF2 46
Patrick S. Fier and John F. Hartwig Ugi Multicomponent Reaction 54
André Boltjes, Haixia Liu, Haiping Liu, and Alexander Dömling Palladium-catalyzed External-CO-Free Reductive Carbonylation of Bromoarenes 66
Hideyuki Konishi, Masataka Fukuda, Tsuyoshi Ueda, and Kei Manabe Practical Syntheses of [2,2′-bipyridine]bis[3,5-difluoro-2- [5-(trifluoromethyl)-2 pyridinyl]phenyl]iridium(III) hexafluorophosphate, [Ir{dF(CF3)ppy}2(bpy)]PF6 and [4,4′-bis (tert-butyl) 2,2′-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate, [Ir{dF(CF3)ppy}2 (dbbpy)]PF6 77
Martins S. Oderinde and Jeffrey W. Johannes (Z)-Enol p-Tosylate Derived from Methyl Acetoacetate: A Useful Cross-coupling Partner for the Synthesis of Methyl (Z)-3-Phenyl (or Aryl)-2-butenoate 93
Yuichiro Ashida, Hidefumi Nakatsuji, and Yoo Tanabe Synthesis of Allenyl Mesylate by a Johnson-Claisen Rearrangement. Preparation of 3-(((tert-butyldiphenyl- silyl)oxy)methyl)penta-3,4-dien-1-yl methanesulfonate 109
Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond Rhodium(I)-catalyzed Allenic Pauson–Khand Reaction 123
Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond Dirhodium (II) tetrakis[N-4-bromo-1,8-naphthoyl-(S)-tert-leucinate] 136
Hélène Lebel, Henri Piras, and Johan Bartholoméüs Buta-2,3-dien-1-ol 153
Hongwen Luo, Dengke Ma, and Shengming Ma Fragment Coupling and Formation of Quaternary Carbons by Visible-Light Photoredox Catalyzed Reaction of tert-Alkyl Hemioxalate Salts and Michael Acceptors 167
Christopher R. Jamison, Yuriy Slutskyy, and Larry E. Overman N-Methoxy-N-methylcyanoformamide 184
Jeremy Nugent and Brett D. Schwartz 4-Cyano-2-methoxybenzenesulfonyl Chloride 198
Elliott D. Bayle, Niall Igoe, and Paul V. Fish Preparation of N-Trifluoromethylthiosaccharin: A Shelf-Stable Electrophilic Reagent for Trifluoromethylthiolation 217
Jiansheng Zhu, Chunhui Xu, Chunfa Xu, and Qilong Shen Homologation of Boronic Esters with Lithiated Epoxides 234
Roly J. Armstrong and Varinder K. Aggarwal Asymmetric Michael Reaction of Aldehydes and Nitroalkenes 252
Yujiro Hayashi and Shin Ogasawara Preparation of anti-1,3-Amino Alcohol Derivatives Through an Asymmetric Aldol-Tishchenko Reaction of Sulfinimines 259
Pamela Mackey, Rafael Cano, Vera M. Foley, and Gerard P. McGlacken Rhenium-Catalyzed ortho-Alkylation of Phenols 280
Yoichiro Kuninobu, Masaki, Yamamoto, Mitsumi Nishi, Tomoyuki Yamamoto, Takashi Matsuki, Masahito Murai, and Kazuhiko Takai Enantioselective Preparation of 5-Oxo-5,6-dihydro-2H-pyran-2-yl phenylacetate via organocatalytic Dynamic Kinetic Asymmetric Transformation (DyKAT) 292
Tamas Benkovics, Adrian Ortiz, Gregory L. Beutner, and Chris Sfouggatakis Preparation of Sodium Heptadecyl Sulfate (Tergitol-7i) 303
Brent A. Banasik and Mansour Samadpour Catalytic Enantioselective Addition of Diethyl Phosphite to N-Thiophosphinoyl Ketimines: Preparation of (R)-Diethyl (1-Amino-1-phenylethyl)phosphonate 313
Shaoquan Lin, Yasunari Otsuka, Liang Yin, Naoya Kumagai, and Masakatsu Shibasaki Water-promoted, Open-flask Synthesis of Amine-boranes: 2-Methylpyridine-borane (2-Picoline-borane) 332
Ameya S. Kulkarni and P. Veeraraghavan Ramachandran Preparation of N-Sulfinyl Aldimines using Pyrrolidine as Catalyst via Iminium Ion Activation 346
Sara Morales, Alfonso García Rubia, Eduardo Rodrigo, José Luis Aceña, José Luis García Ruano, and M. Belén Cid Synthesis of N-Boc-N-Hydroxymethyl-L-phenylalaninal 358
Jae Won Yoo, Youngran Seo, Dongwon Yoo, and Young Gyu Kim Synthesis of Methyl trans-Oxazolidine-5-carboxylate, a Chiral Synthon for threo-β-Amino-α-hydroxy Acid 372
Youngran Seo, Jae Won Yoo, Yoonjae Lee, Boram Lee, Bonghyun Kim, and Young Gyu Kim Preparation of Benzyl((R)-2-(4-(benzyloxy)phenyl)-2-((tert- butoxycarbonyl)amino)acetyl)-D-phenylalaninate using Umpolung Amide Synthesis 388
Matthew T. Knowe, Sergey V. Tsukanov, and Jeffrey N. Johnston

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