Organic Chemistry: Breakthroughs and Perspectives

Organic Chemistry: Breakthroughs and Perspectives

By: Li-Xin Dai (editor), Kuiling Ding (editor)Paperback

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Description

This helpful, useful, practical book presents the most important achievements in organic chemistry over the past decade, summarizing such major developments as C-H activation, organocatalysis, and supramolecular chemistry. Each chapter contains two or three personal, hitherto unpublished, commentaries by leading experts on the topic. This reference work focuses on four main areas: the total synthesis of natural products and chemical biology; synthetic methodology; physical organic chemistry and chemistry relevant to meeting the urgent needs of humanity. The result is a complete and extremely useful source of a wide variety of information for graduate students, post-docs and researchers.

About Author

Kuiling Ding received his B.S. degree from Zhengzhou University (1985) and a Ph.D. from Nanjing University (1990). He was a faculty member of Zhengzhou University from 1990 to 1998. He was engaged in postdoctoral research at Ryukoku University during 1993-1994. He spent another year at TIT as a UNESCO research fellow before joined the faculty of the Shanghai Institute of Organic Chemistry (SIOC) in 1999, where he is currently a professor of organic chemistry and director of SIOC. His research interests include the development of new methodologies and chiral catalysts for asymmetric reactions. Professor Ding has co-authored over 100 scientific publications and fourteen patents. He has also received numerous scientific awards, including the National Natural Science Award of China, Shanghai Peony Award for Natural Science and Eli Lilly Scientific Excellence Award in Chemistry. He is currently serving the International Advisory Board of several journals including Eur. J. Org. Chem, Asian J. Org. Chem., Chem. Commun., Adv. Synth. Cat., Curr. Org. Synth. and ChemPlusChem., as well as the editorial board of Catal. Sci. Tech. Li-Xin Dai is Professor at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. He graduated from Zhejiang University in 1947 and joined the SIOC in 1953. He is the Honorary President of Shanghai Society of Chemistry and Chemical Industry, the Academic Committee Board Member of SIOC and the Honorary Board Member of Asian Journal of Organic Chemistry. His research interests include the design of chiral ligands and their applications in asymmetric catalysis. He was elected as the Member of the Chinese Academy of Sciences in 1993. He has co-authored over 150 scientific publications and has received numerous scientific awards, including Ho Leung Ho Lee Prize and the National Natural Science Award of China.

Contents

List of Contributors XXIII Introduction XXXV 1 Diversity-Oriented Syntheses of Natural Products and Natural Product-Like Compounds 1 Ling-Min Xu, Yu-Fan Liang, Qin-Da Ye, and Zhen Yang 1.1 Introduction 1 1.2 Diversity-Oriented Synthesis (DOS) 2 1.3 Diverted Total Synthesis (DTS) 7 1.4 Function-Oriented Synthesis (FOS) 9 1.5 Target-Oriented Synthesis (TOS) 11 1.6 Conclusion and Perspectives 24 Acknowledgments 26 References 26 Commentary Part 28 Comment 1 28 Michael Foley Comment 2 29 Scott A. Snyder Comment 3 30 Da-Wei Ma Authors Response to the Commentaries 31 References 31 2 Total Synthesis of Natural Products and the Synergy with Synthetic Methodology 33 Qian Wang and Jie-Ping Zhu 2.1 Introduction 33 2.2 Domino Process 36 2.3 Multicomponent Reactions 43 2.4 Oxidative Anion Coupling 52 2.5 Pattern Recognition 60 2.6 Conformation-Directed Cyclization 65 2.7 Conclusion and Perspectives 69 Acknowledgments 70 References 70 Commentary Part 72 Comment 1 72 Kyriacos C. Nicolaou Comment 2 73 Henry N.C. Wong Comment 3 75 Wei-Dong Li References 77 3 Interplay Between the Chemical Space and the Biological Space 81 Ren-Xiao Wang 3.1 Chemical Biology: Historical and Philosophical Aspects 81 3.2 Preparation of Chemical Libraries 90 3.3 Screening Strategies 95 3.4 Target Elucidation and Validation 106 3.5 Conclusion and Perspectives 116 References 117 Commentary Part 121 Comment 1 121 Ke Ding Comment 2 121 Li-He Zhang Comment 3 122 Jun-Ying Yuan Author s Response to the Commentaries 122 References 123 4 Biosynthesis of Pharmaceutical Natural Products and Their Pathway Engineering 125 Michael J. Smanski, Xu-Dong Qu, Wen Liu, and Ben Shen 4.1 Introduction 125 4.2 Expanded Paradigms in Biosynthetic Logic 126 4.3 New Approaches to NP Biosynthesis Research 147 4.4 Better Understanding of the Scope and Diversity of NP Production 156 4.5 Future Perspectives 168 Acknowledgments 170 Abbreviations 171 References 171 Commentary Part 178 Comment 1 178 Yi Tang Comment 2 178 Yi Yu and Zi-Xin Deng Authors Response to the Commentaries 179 Response to Yi Tang 179 Response to Yi Yu and Zixin Deng 179 5 Carbohydrate Synthesis Towards Glycobiology 181 Biao Yu and Lai-Xi Wang 5.1 Introduction 181 5.2 Advances in Chemical Glycosylation 182 5.3 New Strategies in Oligosaccharide Assembly 189 5.4 Enzymatic and Chemoenzymatic Methods 193 5.5 Synthesis of Heparin and Heparan Sulfate Oligosaccharides 195 5.6 Synthesis of Homogeneous Glycoproteins 200 5.7 Synthesis of Carbohydrate-Containing Complex Natural Compounds 206 5.8 Conclusion and Perspectives 212 Acknowledgments 212 References 212 Commentary Part 218 Comment 1 218 Sam Danishefsky Comment 2 218 David Crich Authors Response to the Commentaries 219 References 219 6 Chemical Synthesis of Proteins 221 Lei Liu 6.1 Introduction 221 6.2 Brief History 222 6.3 Current Technology 227 6.4 Applications 236 6.5 Conclusion and Perspectives 242 References 242 Commentary Part 244 Comment 1 244 Sam Danishefsky Comment 2 244 David Crich References 245 7 CuAAC: the Quintessential Click Reaction 247 Valery V. Fokin 7.1 Introduction 247 7.2 Azide Alkyne Cycloaddition: the Basics 249 7.3 CuAAC: Catalysts and Ligands 251 7.4 Mechanistic Aspects of the CuAAC 258 7.5 Reactions of 1-Iodoalkynes 264 7.6 Examples of Application of the CuAAC Reaction 266 7.7 Reactions of Sulfonyl Azides 269 7.8 Outlook/Perspective 273 Acknowledgments 273 References 273 Commentary Part 276 Comment 1 276 Krzysztof Matyjaszewski References 276 8 Transition Metal-Catalyzed C H Functionalization: Synthetically Enabling Reactions for Building Molecular Complexity 279 Keary M. Engle and Jin-Quan Yu 8.1 Introduction 279 8.2 Background and Early Work 281 8.3 First Functionalization: Challenges in Hydrocarbon Chemistry 293 8.4 Further Functionalization: C H Bonds as Reaction Partners in Organic Synthesis 300 8.5 Catalytic C H Functionalization via Metal Insertion 303 8.6 Other Emerging Metal-Catalyzed Further Functionalization Methods 311 8.7 Outlook and Conclusion 321 Acknowledgments 322 Abbreviations 322 References 323 Commentary Part 328 Comment 1 328 Huw M.L. Davies Comment 2 329 Zhenfeng Xi Comment 3 330 Shu-Li You Comment 4 332 Zhang-Jie Shi Authors Response to the Commentaries 333 References 333 9 An Overview of Recent Developments in Metal-Catalyzed Asymmetric Transformations 335 Christian A. Sandoval and Ryoji Noyori 9.1 Introduction 335 9.2 Asymmetric Carbon Carbon Bond Formation 336 9.3 Asymmetric Reductions and Oxidations 348 9.4 Conclusion 353 References 353 Commentary Part 363 Comment 1 363 Qi-Lin Zhou Comment 2 363 Andreas Pfaltz Comment 3 365 Xue-Long Hou Comment 4 365 Hisashi Yamamoto References 366 10 The Proline-Catalyzed Mannich Reaction and the Advent of Enamine Catalysis 367 Benjamin List and Sai-Hu Liao 10.1 Introduction 367 10.2 The Proline-Catalyzed Mannich Reaction 367 10.3 Conclusion 374 References 374 Commentary Part 375 Comment 1 375 Seiji Shirakawa and Keiji Maruoka Comment 2 377 The Early Status of Asymmetric Organocatalysis 377 Liu-Zhu Gong Milestone in Asymmetric Organocatalysis 378 Enamine Catalysis 378 Iminium Catalysis 378 Domino Reactions by Amine Catalysis 378 Hydrogen Bonding Catalysis 378 Conclusion 379 Comment 3 379 Wen-Jing Xiao References 382 11 Recent Topics in Cooperative Catalysis: Asymmetric Catalysis, Polymerization, Hydrogen Activation, and Water Splitting 385 Motomu Kanai 11.1 Introduction 385 11.2 Cooperative Catalysis in Asymmetric Reactions 387 11.3 Cooperative Catalysis in Alkene Polymerization 393 11.4 Cooperative Catalysis in Hydrogen Activation/Generation 394 11.5 Conclusion and Perspectives 398 References 398 Commentary Part 401 Comment 1 401 Takao Ikariya Comment 2 402 Takashi Ooi Comment 3 405 Kuiling Ding Comment 4 409 David Milstein Authors Response to the Commentaries 410 References 411 12 Flourishing Frontiers in Organofluorine Chemistry 413 G. K. Surya Prakash and Fang Wang 12.1 Introduction 413 12.2 Synthetic Approaches for the Introduction of Fluorine-Containing Functionalities and Related Chemistry 415 12.3 Conclusion and Perspectives 459 Acknowledgment 460 References 460 Commentary Part 470 Comment 1 470 David O Hagan Comment 2 471 Jinbo Hu Comment 3 472 Kuiling Ding and Li-Xin Dai Authors Response to the Commentaries 472 References 473 Addendum 473 13 Supramolecular Organic Chemistry: the Foldamer Approach 477 Zhan-Ting Li 13.1 Introduction 477 13.2 Foldamers: the Background 479 13.3 Molecular Recognition 480 13.4 Homoduplex 497 13.5 Organogels 499 13.6 Vesicles 501 13.7 Supramolecular Liquid Crystals 502 13.8 Macrocycles 503 13.9 Catalysis 510 13.10 Macromolecular Self-Assembly 514 13.11 Conclusion and Perspectives 516 Acknowledgments 517 References 517 Commentary Part 520 Comment 1 520 Peter J. Stang Comment 2 521 Liang Zhao and Mei-Xiang Wang Introduction 521 Macrocyclic Compounds 522 Cycloparaphenylenes 522 Pillar[n]arenes 524 Heteracalixaromatics 525 Noncovalent Interactions 527 Quadruple Hydrogen Bonding 527 Halogen Bonding 528 Anion Interaction 529 Perspectives 530 Acknowledgements 531 Comment 3 531 Chen-Ho Tung Author s Response to the Commentaries 532 Reply to Zhao and Wang s Comments 532 Reply to Tung s Comments 533 Reply to Stang s Comments 533 References 533 14 Novel Catalysis for Alkene Polymerization Mediated by Post-Metallocenes: a Gateway to New Polyalkenes 537 Hiromu Kaneyoshi, Haruyuki Makio, and Terunori Fujita 14.1 Introduction 537 14.2 Late Transition Metal Complexes 538 14.3 Early Transition Metal Complexes 544 14.3.1 Phenoxyimine-Ligated Group 4 Metal Complexes 544 14.4 Conclusion and Perspectives 553 Acknowledgment 554 References 554 Commentary Part 555 Comment 1 555 Robert Grubbs Comment 2 556 Jun Okuda General 556 Early Work on Late Metals 556 Ligand Design Principles for Post-metallocenes 556 Comment 3 557 Eugene Y.-X. Chen Authors Response to the Commentaries 559 References 559 15 Chem Is Try Computationally and Experimentally: How Will Computational Organic Chemistry Impact Organic Theories, Mechanisms, and Synthesis in the Twenty-First Century? 561 Zhi-Xiang Yu and Yong Liang 15.1 Introduction 561 15.2 Developing New Theories, Concepts, and Understandings for Organic Chemistry 561 15.3 Understanding Reaction Mechanisms 571 15.4 Computation-Guided Development of New Catalysts, New Reactions, and Synthesis Planning for Ideal Synthesis 583 15.5 Conclusion 595 Acknowledgments 597 References 597 Commentary Part 600 Comment 1 600 K. N. Houk Comment 2 600 Yun-Dong Wu and Xin-Hao Zhang References 601 16 Case Study of Mechanisms in Synthetic Reactions 603 Ai-Wen Lei and Li-Qun Jin 16.1 Introduction 603 16.2 Mechanistic Study of Coupling Reactions 604 16.3 Mechanistic Study of Aerobic Oxidation 627 16.4 Conclusion and Perspective 634 Acknowledgments 635 References 635 Commentary Part 638 Comment 1 638 Xin Mu, Guo-Sheng Liu, and Qi-Long Shen Comment 2 640 Yoshinori Yamamoto Authors Response to the Commentaries 640 References 640 17 Organic Materials and Chemistry for Bulk Heterojunction Solar Cells 643 Chun-Hui Duan, Fei Huang, and Yong Cao 17.1 Introduction 643 17.2 Molecular Design and Engineering of Donor Materials 645 17.3 Molecular Design and Engineering of Acceptor Materials 662 17.4 Conclusion and Outlook 671 Acknowledgments 671 References 671 Commentary Part 676 Comment 1 676 Niyazi Serdar Sariciftci Comment 2 677 Yongfang Li Comment 3 681 Guillermo C. Bazan Comment 4 682 Xiong Gong Authors Response to the Commentaries 682 References 682 18 Catalytic Utilization of Carbon Dioxide: Actual Status and Perspectives 685 Albert Boddien, Felix Gartner, Christopher Federsel, Irene Piras, Henrik Junge, Ralf Jackstell, and Matthias Beller 18.1 Introduction 685 18.2 Catalytic Reductions of CO2 to Formic Acid and Methanol 686 18.3 CO2 as a C1-Building Block in C C Coupling Reactions 702 18.4 Catalytic C O Bond Formation Utilizing Carbon Dioxide 703 18.5 Current Industrial Processes Using CO2 710 18.6 Conclusion and Outlook 715 References 716 Commentary Part 722 Comment 1 722 Gabor Laurenczy Comment 2 723 Min Shi References 724 19 Synthetic Chemistry with an Eye on Future Sustainability 725 Guo-Jun Deng and Chao-Jun Li 19.1 Introduction 725 19.2 Cross-Dehydrogenative Coupling 729 19.3 Nucleophilic Addition of Terminal Alkynes in Water 741 19.4 Conclusion and Perspectives 749 Acknowledgments 750 References 750 Commentary Part 754 Comment 1 754 Roger A. Sheldon Comment 2 756 Tak Hang Chan References 758 20 Organic -Conjugated Molecules for Organic Semiconductors and Photovoltaic Materials 759 De-Qing Zhang, Xiao-Wei Zhan, Zhao-Hui Wang, Jian Pei, Guan-Xin Zhang, and Dao-Ben Zhu 20.1 Introduction 759 20.2 Conjugated Molecules for p-Type Organic Semiconductors 760 20.3 Conjugated Molecules for n-Type Organic Semiconductors 766 20.4 Conjugated Molecules for Photovoltaic Materials 769 20.5 Conclusion and Outlook 773 References 774 Commentary Part 777 Comment 1 777 Seth R. Marder Comment 2 777 Tien Yau Luh Authors Response to the Commentaries 779 References 779 21 The Future of Organic Chemistry an Essay 781 Ronald Breslow 21.1 Introduction 781 21.2 The Field of Organic Chemistry Will Broaden 781 21.3 Conclusion 789 Index 791

Product Details

  • ISBN13: 9783527329632
  • Format: Paperback
  • Number Of Pages: 853
  • ID: 9783527329632
  • weight: 1786
  • ISBN10: 3527329633

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