Carbohydrates: Tools for Stereoselective Synthesis

Overview

Closing a gap in the literature, this comprehensive book presents the utility of carbohydrate derivatives as chiral auxiliaries, reagents, complex ligands and organocatalysts, together with details of their preparation, as well as their ...

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Overview

Closing a gap in the literature, this comprehensive book presents the utility of carbohydrate derivatives as chiral auxiliaries, reagents, complex ligands and organocatalysts, together with details of their preparation, as well as their successful application in stereoselective synthesis.

Divided into four parts:
* Carbohydrate Auxiliaries
* Carbohydrate Reagents
* Carbohydrate Ligands
* Carbohydrate Organocatalysts

It is an indispensable source for every organic chemist.

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Product Details

  • ISBN-13: 9783527323791
  • Publisher: Wiley
  • Publication date: 3/25/2013
  • Edition number: 1
  • Pages: 394
  • Product dimensions: 6.90 (w) x 9.70 (h) x 1.00 (d)

Meet the Author

Mike Boysen is Junior Professor at the Leibniz University, Hannover, Germany. He obtained his Ph.D. degree under the guidance of Thisbe K. Lindhorst at th University Kiel. After a postdoctoral fellowship with Stefan Oscarson at Göteborg University he joined the faculty at Hannover University. His research interests include synthetic carbohydrate chemistry, monosaccharide transformation, enantioselective synthesis and development of novel chiral ligands for metal catalysis based on carbohydrates.

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Table of Contents

Foreword XI

Preface XIII

List of Contributors XV

Part I Carbohydrate Auxiliaries 1

1 Reactions of Nucleophiles with Electrophiles Bound to Carbohydrate Auxiliaries 3
Zhiwei Miao

1.1 Introduction 3

1.2 Strecker Reactions 3

1.3 Ugi Reactions 8

1.4 Allylations 13

1.5 Mannich-Type Reactions 15

1.6 Addition of Phosphites 19

1.7 Dynamic Kinetic Resolution of α-Chloro Carboxylic Esters 22

References 24

2 1,4-Addition of Nucleophiles to α,β-Unsaturated Carbonyl Compounds 27
Kiichiro Totani and Kin-ichi Tadano

2.1 Introduction 27

References 45

3 Reaction of Enolates 47
Noureddine Khiar, Inmaculada Fernández, Ana Alcudia, Maria Victoria García and Rocío Recio

3.1 Introduction 47

3.2 Aldol Alkylation 48

3.3 Aldol Addition 56

3.4 Concluding Remarks 60

References 62

4 Cycloadditions 65
Mike M.K. Boysen

4.1 Diels–Alder Reactions 65

4.2 1,3-Diploar Cycloadditions 93

4.3 [2 + 2] Cycloadditions 101

References 104

5 Cyclopropanation 107
Noureddine Khiar, Inmaculada Fernández, Ana Alcudia, Maria Victoria García and Rocío Recio

5.1 Introduction 107

5.2 Epoxidation 113

5.3 Construction of Chiral Sulfur and Phosphorus Centers 117

5.4 Chiral Phosphorus Compounds 120

5.5 Concluding Remarks 122

References 123

Part II Carbohydrate Reagents 125

6 Hydride Reductions and 1,2-Additions of Nucleophiles to Carbonyl Compounds Using Carbohydrate-Based Reagents and Additives 127
Omar Boutureira and Benjamin G. Davis

6.1 Introduction 127

6.2 Hydride Reductions 127

6.3 1,2-Additions of Nucleophiles to Carbonyl Compounds 135

References 140

7 Aldol-Type Reactions 143
Inmaculada Fernández, Noureddine Khiar, Ana Alcudia, Maria Victoria García and Rocío Recio

7.1 Introduction 143

7.2 Titanium Lewis Acids for Enolate Formation 143

7.3 1,2-Additions of Nucleophiles to Carbonyl Compounds Using Stoichiometric Reagents 149

References 153

Part III Carbohydrate Ligands 155

8 Hydrogenation Reactions 157
Carmen Claver, Sergio Castillón, Montserrat Diéguez and Oscar Pàmies

8.1 Introduction 157

8.2 Hydrogenation of C=C and C=N Bonds 158

8.3 P-Donor Ligands 159

8.4 P–N Donors 177

8.5 P–S Donors 178

Acknowledgments 180

References 180

9 Hydroformylations, Hydrovinylations, and Hydrocyanations 183
Mike M.K. Boysen

9.1 Hydroformylation Reactions 183

9.2 Hydrovinylation Reactions 202

9.3 Hydrocyanation Reactions 206

9.4 Hydrosilylation Reactions 211

9.5 Conclusion 214

References 215

10 Carbohydrate-Derived Ligands in Asymmetric Tsuji–Trost Reactions 217
Montserrat Diéguez and Oscar Pàmies

10.1 Introduction 217

10.2 Ligands 220

10.3 Conclusions 242

Acknowledgments 242

References 242

11 Carbohydrate-Derived Ligands in Asymmetric Heck Reactions 245
Montserrat Diéguez and Oscar Pàmies

11.1 Introduction 245

11.2 Ligands 247

11.3 Conclusions 250

Acknowledgments 251

References 251

12 1,4-Addition of Nucleophiles to α,β-Unsaturated Carbonyl Compounds 253
Yolanda Díaz, M. Isabel Matheu, David Benito and Sergio Castillón

12.1 Copper-Catalyzed Reactions – Introduction 253

12.2 Copper-Catalyzed Reactions – Ligands 257

12.3 Enantioselective Copper-Catalyzed 1,4-Addition of Organometallics to α,β-Unsaturated Carbonyl Compounds 266

12.4 Rhodium-Catalyzed Reactions 286

12.5 Conclusions 287

References 288

13 1,2-Addition of Nucleophiles to Carbonyl Compounds 293
M. Isabel Matheu, Yolanda Díaz, Patricia Marcé and Sergio Castillón

13.1 Introduction 293

13.2 Addition of Organometallic Reagents to Aldehydes 294

13.3 Addition of Trimethylsilyl Cyanide to Ketones. P=O,O Ligands 308

13.4 Conclusion 311

References 312

14 Cyclopropanation 313
Mike M.K. Boysen

References 318

Part IV Carbohydrate Organocatalysts 319

15 Oxidations 321
O. Andrea Wong, Brian Nettles and Yian Shi

15.1 Oxidations 321

15.2 Conclusion 346

References 347

16 Enantioselective Addition Reactions Catalyzed by Carbohydrate-Derived Organocatalysts 351
Jun-An Ma and Guang-Wu Zhang

16.1 Introduction 351

16.2 Strecker, Mannich, and Nitro-Mannich Reactions 351

16.3 Michael Additions 358

16.4 Miscellaneous Reactions 364

16.5 Outlook 367

Acknowledgment 368

References 368

Index 371

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