Free download Organic Stereochemistry by Hua-Jie Zhu

Authors of:  Organic Stereochemistry by Hua-Jie Zhu

Hua-Jie Zhu

Table of Contents in  Organic Stereochemistry by Hua-Jie Zhu

Contents

Preface IX

Acknowledgments XI

List of Abbreviations XIII

Part I Fundamentals

1 Chirality

1.1 Introduction

1.2 Tetrahedron of Carbon

1.2.1 Terpenoids

1.2.2 Flavonoids

1.2.3 Alkaloids

1.2.4 Steroids

1.2.5 Glycosides

1.2.6 Others

1.3 Other Stereogenic Centers

1.4 Optical Characteristics

1.4.1 Measurement of OR

1.4.2 ECD and Its Definition

1.4.3 Outline of VCD

1.4.4 Outline of ROA

References

2 Non-optical Method in Configuration Study

2.1 13C NMR Spectra

2.1.1 NMR and Atomic Structure

2.1.2 13C NMR Calculation

2.1.3 1H NMR

2.1.4 13C NMR Prediction and Conformational Search

2.2 X-Ray Diffraction and Mosher Method

2.2.1 X-Ray Diffraction 41

2.2.2 Mosher Method 44

2.3 Transition State Energy and Chirality Selectivity 51

www.ebook3000.com

VI Contents

2.4 Separation of Chiral Compounds 53

2.4.1 Chiral Organic Bases 53

2.4.2 Chiral Organic Acids 53

2.4.3 Chiral Organic Alcohols 53

2.4.4 Others 54

References 55

Part II Techniques 57

3 Optical Rotation (Rotatory Dispersion, ORD) 59

3.1 Introduction 59

3.2 Quantum Theory 59

3.3 Matrix Model 63

3.3.1 Matrix Basis 65

3.3.2 Explanation of General OR Characteristics 68

3.3.2.1 Sample Calculations 68

3.3.2.2 Calculated Values in Same Series of Compounds 73

3.4 ORD 77

3.5 Application 77

3.5.1 AC Assignment for Mono-Stereogenic Center Compounds 79

3.5.2 Matrix Model Application 80

3.5.3 AC Assignment for Poly-Stereogenic Center Compounds 82

3.5.4 Using ORD Method 83

References 84

4 Electronic Circular Dichroism 87

4.1 Exciton Chirality CD 87

4.2 ECD Characteristics for Chiral Metallic Compounds 92

4.3 Quantum Theory Basis 94

4.4 Principle Using ECD 95

4.5 Application 97

4.5.1 Procedure to Do ECD 97

4.5.2 ECD Application 97

4.5.3 UV Correction 102

References 105

5 Vibrational Circular Dichroism and Raman Optical Activity 107

5.1 Exciton Chirality 108

5.2 Quantum Theory Basis 109

5.2.1 VCD and IR 109

5.2.2 ROA and Raman Scattering 110

5.3 Principles Using VCD and ROA 113

5.4 Application 115

5.4.1 VCD Application 115

www.ebook3000.com

Contents VII

5.4.2 ROA Application 124

References 126

6 Combinational Use of Different Methods 129

6.1 Tactics to Select Methods 129

6.1.1 13C NMR Methods 130

6.1.2 OR and ORD 131

6.1.3 Matrix 132

6.1.4 ECD 132

6.1.5 VCD Method 133

6.2 Examples and Discussion 133

6.3 Revised Structures 138

6.3.1 ORD Method 139

6.3.2 Combinational Use of OR and ECD 144

6.3.3 VCD and ECD 146

6.3.4 Comprehensive Use of OR, ECD, and VCD 147

References 160

Part III Reactions 163

7 Enantioselective Reaction 165

7.1 Enantioselective Addition 165

7.1.1 Organic Zn- or Zn-Ti Reagent 165

7.1.2 Organic Cu–Zn, Cu–Li Reagent 169

7.1.3 Organo-Fe Complexes 173

7.1.4 Other Organo-Metallic Complexes 175

7.1.5 Organo-Si Reagents 178

7.2 Enantioselective Reduction 178

7.2.1 Green Chemistry 181

7.3 Enantioselective Oxidation 184

7.4 Prediction of ee Using Calculations 185

7.5 Catalyst Types 189

7.5.1 Amino Alcohols 189

7.5.2 Chiral Ligands Containing N–O Group 190

7.5.3 Chiral Axial Catalysts 191

7.5.4 Solid-Supported Chiral Compounds 192

7.5.5 Spiral Chiral Compounds 193

7.5.6 Asymmetric-Axle-Supported Chiral Catalyst 194

7.5.7 Chiral Shiff-Base Ligands 195

7.5.8 Some Asymmetric Lewis Acids 196

7.5.9 Organic P-Containing Ligands 197

7.6 Three Phenomena 198

7.6.1 Chirality Amplification (Nonlinear Effect) 198

7.6.2 Auto-Self Catalysis 199

www.ebook3000.com

VIII Contents

7.6.3 Odd–Even Carbon Effect 199

References 201

8 Chemoselective Reaction 205

8.1 Chemoselective Additions 205

8.1.1 Addition to C=O or C=C Groups

8.2 Chemoselective Reduction

8.3 Chemoselective Oxidation

8.4 Other Chemoselective Reactions

References

9 Stereoselective Reaction

9.1 Conformational Study

9.2 Effect of Conformation on Reactions

9.3 Regioselective Reactions

9.4 Diastereoselective Reactions

9.4.1 Diastereoselective Additions

9.4.2 Other Diastereoselective Reactions

9.5 Calculation Using Theoretical Protocol

References

10 Total Organic Synthesis

10.1 Introduction

10.2 Retrosynthesis Strategies

10.3 Examples in Synthesis

10.3.1 (+)-Hirsutene

10.3.2 (2R,3S)-Rubiginone A2 and Its Analog

10.3.3 (+)-Brefeldin A

10.3.4 Malyngamide U and Its AC Reassignment

10.3.5 Taxol Derivatives

10.3.6 Amphidinolide T2 and Its Derivatives

10.3.7 (+)-Vindoline

10.4 Calculation in Total Synthesis

References

Index

File Size: 3.98 MB. Pages: 337 Please read Disclaimer.

Free download  Organic Stereochemistry by Hua-Jie Zhu

Download Link

You may also like to download “Organic Chemistry 9e by Leroy G. Wade JR”.

Free download hundreds of chemistry books in pdf from HERE.

Please Subscribe to our Email list and get notified of our latest uploads (Books, documents) and new updates. Email Subscription Box is provided on the sidebar (for PC) and on the bottom of this post (for Android Devices).

Kindly Like, Follow, and Share our social media pages so that the maximum number of people can benefit from this public service!

Facebook   Instagram    LinkedIn    Twitter    Pinterest

P.S: If the download link(s) is/are not working, kindly drop a comment below, so we’ll update the download link for you.

Happy reading!