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Produktbild: Atropisomerism in Asymmetric Organic Synthesis
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Atropisomerism in Asymmetric Organic Synthesis Challenges and Applications

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Beschreibung

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

04.12.2024

Abbildungen

farbige Illustrationen

Herausgeber

Shinobu Takizawa + weitere

Verlag

Wiley-VCH

Seitenzahl

352

Maße (L/B/H)

24,5/17,2/2,5 cm

Gewicht

666 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-3-527-35283-8

Beschreibung

Portrait

Shinobu Takizawa is Associate Professor at the Institute of Scientific and Industrial Research (SANKEN) and AI Research Center at Osaka University (Japan). He received his Ph.D. in chemistry at the Graduate School of Pharmaceutical Science, Osaka University in 2000. From 2006 to 2008 he did postdoctoral studies at The Scripps Research Institute (USA) with Professor Dale L. Boger. He received the Daiichi Pharmaceutical Co. Ltd. Award in Synthetic Organic Chemistry, Japan (2000), the Pharmaceutical Society of Japan Award for Young Scientists (2009), the Daiichi-Sankyo Co. Ltd. Award in Synthetic Organic Chemistry, Japan (2009), the Osaka University Presidential Award for Encouragement in Research (2015) and the Pharmaceutical Society of Japan Award for Divisional Scientific Promotion (2019). His current research interest focuses on developing sustainable synthetic reactions with machine learning optimization. He is the author of more than 125 articles.

Mohamed Salem is a research associate at the Institute of Scientific and Industrial Research at Osaka University. He graduated from the Faculty of Pharmacy, Suez Canal University (Egypt) in 2017, and received his Ph.D. in chemistry at the Graduate School of Science, Osaka University in 2022 under the direction of Professor Hiroaki Sasai and Professor Takayoshi Suzuki. Mohamed was awarded the Japanese Government Scholarship (MEXT) in 2019. His current research interest is designing and synthesizing CPL-responsive SOMs using electrochemistry, machine-learning-assisted optimization of reaction parameters, and asymmetric catalysis.

Produktdetails

Einband

Gebundene Ausgabe

Erscheinungsdatum

04.12.2024

Abbildungen

farbige Illustrationen

Herausgeber

Verlag

Wiley-VCH

Seitenzahl

352

Maße (L/B/H)

24,5/17,2/2,5 cm

Gewicht

666 g

Auflage

1. Auflage

Sprache

Englisch

ISBN

978-3-527-35283-8

Herstelleradresse

Wiley-VCH GmbH
Boschstraße 12
69469 Weinheim
DE

Email: wiley-vch@kolibri360.de

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  • Produktbild: Atropisomerism in Asymmetric Organic Synthesis
  • Preface xiii

    About the Editors xv

    Part I Atroposelective Synthesis 1

    1 Introduction 3
    Mohamed S. H. Salem and Shinobu Takizawa

    1.1 Molecular Chirality and Atropisomerism 3

    1.2 Atropisomerism in Asymmetric Organic Synthesis 6

    1.3 Atropisomerism: Challenges and Applications 10

    References 16

    2 Iron- and Ruthenium-Catalyzed Atroposelective Synthesis of Axially Chiral Compounds 21
    Tatsuya Uchida

    2.1 Introduction 21

    2.2 Oxidative Homo-coupling of 2-Naphthols to BINOL and Its Derivatives 22

    2.3 Oxidative Cross-coupling of 2-Naphthols to Asymmetric BINOLs 29

    2.4 Oxidative Spirocyclization of 2-Naphthols 38

    2.5 Conclusion 41

    References 42

    3 Vanadium-Catalyzed Atroposelective Coupling of Arenols and Application in the Synthesis of Polycyclic Heteroaromatics (PHAs) 45
    Mohamed S. H. Salem and Shinobu Takizawa

    3.1 Introduction 45

    3.2 Chiral Vanadium Catalysis in Homo-Coupling of Hydroxycarbazoles 47

    3.3 Chiral Vanadium Catalysis in Hetero-Coupling of Hydroxycarbazole with 2-Naphthols 50

    3.4 Enantioselective Synthesis of Oxa[9]helicenes via Chiral Vanadium Complex-Catalyzed Homo-Couplings of Polycyclic Phenols 55

    3.5 Enantioselective Synthesis of Oxaza[7]dehydrohelicenes via Chiral Vanadium Complex-Catalyzed Hetero-Couplings of

    3-Hydroxycarbazoles and 2-Naphthols 58

    3.6 Summary and Conclusion 62

    References 63

    4 Atroposelective Suzuki-Miyaura Coupling Toward Axially Chiral Biaryls: Mechanistic Insight 69
    Toshinobu Korenaga

    4.1 Introduction 69

    4.2 Mechanism Insight of SMC Reaction and Enantiodetermining Step 70

    4.3 Asymmetric SMC Reaction 72

    4.4 Conclusion 85

    References 85

    5 Organocatalytic Enantioselective Formation of Atropisomers 91
    Chiara Portolani, Giovanni Centonze, and Giorgio Bencivenni

    5.1 Introduction 91

    5.2 Aminocatalysis 92

    5.3 Brønsted Base Catalysis 99

    5.4 Phase Transfer Catalysis 112

    5.5 Chiral Phosphoric Acids 120

    5.6 Conclusions 131

    References 132

    6 Synthesis of Atropisomers via Enantioselective Ring-Opening Reactions 137
    Longhui Duan and Zhenhua Gu

    6.1 Introduction 137

    6.2 Asymmetric Ring Opening of Biaryl Lactones and Their Derivatives 137

    6.3 Asymmetric Ring-Opening Reactions via C-I Bond Cleavage 145

    6.4 Asymmetric Ring-Opening Reactions via C-N and C-P Bonds Cleavage 153

    6.5 Asymmetric Ring-Opening Reactions via C-C and C-Si Bond Cleavage 155

    6.6 Asymmetric Ring-Opening Reactions via C-O and C-S Bond Cleavage 159

    6.7 Oriented Asymmetric Ring Opening via Transient Pentacyclic Metal Species 162

    6.8 Summary and Conclusions 164

    References 164

    Part II Challenges and Applications 171

    7 Axially Chiral Ligands and Catalysts Derived from Atropisomeric Binaphthyl Structures 173
    Shouyi Cen and Zhipeng Zhang

    7.1 Introduction 173

    7.2 Chiral Ligands Derived from BINOLs 174

    7.3 Chiral Ligands Derived from BINAMs 185

    7.4 Chiral Ligands Derived from NOBINs 187

    7.5 Chiral Organocatalysts Derived from BINOLs 189

    7.6 Chiral Organocatalysts Derived from BINAMs 197

    7.7 Chiral Organocatalysts Derived from NOBINs 199

    7.8 Chiral Ligands and Catalysts Derived from Other Binaphthyl Motifs 199

    7.9 Summary and Outlook 201

    References 202

    8 Multinuclear Zinc Catalysts with Axial Chirality 219
    Takayoshi Arai

    8.1 Pioneering Works on BINOL-Zn System 219

    8.2 Enantioselective Addition Reaction of Dialkylzinc to Aldehydes Using BINOL Additive 219

    8.3 Catalytic Asymmetric Alkynylation of Aldehydes 223

    8.4 Catalytic Asymmetric Diels-Alder Reaction 224

    8.5 Catalytic Asymmetric Epoxidation of Enones 225

    8.6 Catalytic Asymmetric Direct Aldol Reaction 226

    8.7 Catalytic Asymmetric Iodofunctionalization of Alkenes 230

    8.8 Conclusions 233

    References 233

    9 Binaphthyl-Based Chiral DMAP Derivatives in Enantioselective Transformations 237
    Hiroki Mandai and Seiji Suga

    9.1 Introduction 237

    9.2 Binaphthyl-Based Chiral DMAP Derivatives 240

    9.3 Intramolecular Acyl Transfer Reactions 242

    9.4 Intermolecular Acyl Transfer Reactions 247

    9.5 Summary and Conclusions 260

    References 261

    10 Catalytic Atroposelective Oxidative Coupling in Natural Product Synthesis 267
    Houng Kang and Marisa C. Kozlowski

    10.1 Introduction 267

    10.2 Copper-Catalyzed Asymmetric Oxidative Coupling to Construct a Chiral Axis 273

    10.3 Vanadium-Catalyzed Asymmetric Oxidative Coupling to Construct a Chiral Axis 283

    10.4 Enzymatic Strategies to Synthesize Natural Products via Atroposelective Coupling 295

    10.5 Conclusion 297

    References 298

    11 Atropisomerism in Drug Discovery and Development 309
    KhaledM.Darwish,AsmaaS.A.Yassen,EbtehalM.Husseiny, Mohammed I. A. Hamed, and Mohamed A. Helal

    11.1 Introduction 309

    11.2 Configuration Assignment of Atropisomeric Drugs 309

    11.3 Classification of Atropisomeric Drugs According to the Rotational Energy Barrier 310

    11.4 Analysis of Atropisomeric Drugs Across the Pharmaceutical Market 311

    11.5 Introducing Atroisomerism to Modulate Selectivity 320

    11.6 Challenges for Atropisomerism within Drug Discovery 323

    11.7 Conclusion 326

    References 326

    Index 331