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Asymmetric Bronsted Acid Catalysis

Asymmetric Bronsted Acid Catalysis

Magnus Rueping, Dixit Parmar, Erli Sugiono

ISBN: 978-3-527-69479-2

Nov 2015

240 pages

$140.99

Description

A much-needed overview of the synthesis of chiral Brønsted acids and their applications in various organic transformations.
The internationally recognized and highly respected expert authors summarize the most significant advances in this new and dynamically progressing field, with a special emphasis on BINOL-derived phosphoric acids. They also describe other catalysts, such as C-H, TADDOL-derived Brønsted, and sulfonic acids. For easy navigation, the chapters are organized in the first instance according to reactive intermediate and then sub-divided by reaction type.
An appendix with selected experimental details for benign and straight-forward procedures rounds of the book, making this the number-one information source for organic chemists in academia and industry.

Preface IX

1 Introduction 1

1.1 Book Structure and Notation 1

1.2 Catalyst Preparation 2

1.3 Metal Impurities 3

References 3

2 Reactions of Imines 5

2.1 Nucleophilic Addition Reactions 5

2.1.1 C-Nucleophiles 5

2.1.2 N-Nucleophiles 17

2.1.3 O-Nucleophiles 20

2.1.4 P-Nucleophiles 21

2.2 Mannich Reactions 24

2.3 Strecker Reactions 28

2.4 Biginelli Reactions 31

2.5 Friedel–Crafts Reactions 33

2.5.1 Indole Coupling Partners with Aldimines 33

2.5.2 Indole Coupling Partners to Ketimines 35

2.5.3 Non-Indole Aromatic Partners 38

2.5.4 Pictet–Spengler Reactions 41

2.6 Transfer Hydrogenations 44

2.6.1 Imine Partners 44

2.6.2 α-Imino Ester Partners 49

2.6.3 N-Heterocycles 51

2.6.4 Cascade Processes 56

2.6.5 Miscellaneous Reactions 61

2.7 Pericyclic Reactions 63

2.7.1 Aza-Diels–Alder/Povarov 63

2.7.2 1,3-Dipolar Cycloaddition 69

2.7.3 Electrocyclizations and Sigmatropic Rearrangements 72

2.8 Radical Reactions 77

References 79

3 Reactions of Generated Imine Intermediates 87

3.1 Enamines 87

3.1.1 Nucleophilic Addition Reactions 87

3.1.2 Transfer Hydrogenation 90

3.2 Indoles Containing Leaving Groups 91

3.2.1 Nucleophilic Addition Reactions 92

3.2.2 Friedel–Crafts Reactions 96

3.3 N-Acetals and Aminals 99

3.3.1 Nucleophilic Addition Reactions 99

3.3.2 Friedel–Crafts Reactions 104

3.3.3 Transfer Hydrogenation 105

3.4 Miscellaneous Formation 111

References 115

4 Reactions of Carbonyls 117

4.1 Nucleophilic Addition Reactions 117

4.1.1 C-Nucleophiles 117

4.1.2 N-, O-, and P-Nucleophiles 124

4.2 Aldol Reactions 133

4.3 Pericyclic Reactions 137

4.4 Reductions 140

References 142

5 Reactions of Generated Carbonyl Intermediates 145

5.1 Enol Ethers 145

5.2 Acetals 149

5.3 Phenols Containing Leaving Groups 153

References 158

6 Reactions of Alkenes 161

6.1 Nucleophilic Addition Reactions 161

6.2 Friedel–Crafts Reactions 169

6.3 Pericyclic Reactions 172

6.4 Cascades 177

References 180

7 Reactions of Other Substrates 183

7.1 Aziridines 183

7.2 O-Heterocycles and Ethers 185

7.3 Hydrazines and Hydrazones 190

7.4 Azo/Diazo Substrates 192

7.5 Halogens 198

7.5.1 Fluorine 198

7.5.2 Bromine 203

7.6 Oxidizing Agents 206

7.7 Miscellaneous Substrates 209

References 212

Experimental Protocols 215

Appendix A: Catalyst Frequency 215

Appendix B: Overview of Phosphoric Acids (PA) 217

Appendix C: Overview of N-Phosphoramide Acids (NPA) 221

Appendix D: Overview of SPINOL Phosphoric Acids (SPA) 223

Appendix E: Overview of All Other Brønsted Acids (BA) 225

Index 229