Organic stereochemistry : experimental and computational methods / Hua-Jie Zhu.

Format:

Book

Author/Creator:

Zhu, Hua-Jie, author.

Language:

English

Subjects (All):

Stereochemistry.

Physical organic chemistry.

Physical Description:

1 online resource (337 p.)

Edition:

1st ed.

Place of Publication:

Weinheim an der Bergstrasse, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2015.

Language Note:

English

Summary:

Adopting a novel approach to the topic by combining theoretical knowledge and practical results, this book presents the most popular and useful computational and experimental methods applied for studying the stereochemistry of chemical reactions and compounds. The text is clearly divided into three sections on fundamentals, spectroscopic and computational techniques, and applications in organic synthesis. The first part provides a brief introduction to the field of chirality and stereochemistry, while the second part covers the different methodologies, such as optical rotation, electronic circular dichroism, vibrational circular dicroism, and Raman spectroscopy. The third section then goes on to describe selective examples in organic synthesis, classified by reaction type, i.e. enantioselective, chemoselective and stereoselective reactions. A final chapter on total synthesis of natural products rounds off the book. A valuable reference for researchers in academia and industry working in the field of organic synthesis, computational chemistry, spectroscopy or medicinal chemistry.

Contents:

Cover; Title Page; Copyright; Contents; Preface; Acknowledgments; List of Abbreviations; Part I Fundamentals; Chapter 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; Chapter 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 Search2.2 X-Ray Diffraction and Mosher Method; 2.2.1 X-Ray Diffraction; 2.2.2 Mosher Method; 2.3 Transition State Energy and Chirality Selectivity; 2.4 Separation of Chiral Compounds; 2.4.1 Chiral Organic Bases; 2.4.2 Chiral Organic Acids; 2.4.3 Chiral Organic Alcohols; 2.4.4 Others; References; Part II Techniques; Chapter 3 Optical Rotation (Rotatory Dispersion, ORD); 3.1 Introduction; 3.2 Quantum Theory; 3.3 Matrix Model; 3.3.1 Matrix Basis; 3.3.2 Explanation of General OR Characteristics; 3.3.2.1 Sample Calculations

3.3.2.2 Calculated Values in Same Series of Compounds3.4 ORD; 3.5 Application; 3.5.1 AC Assignment for Mono-Stereogenic Center Compounds; 3.5.2 Matrix Model Application; 3.5.3 AC Assignment for Poly-Stereogenic Center Compounds; 3.5.4 Using ORD Method; References; Chapter 4 Electronic Circular Dichroism; 4.1 Exciton Chirality CD; 4.2 ECD Characteristics for Chiral Metallic Compounds; 4.3 Quantum Theory Basis; 4.4 Principle Using ECD; 4.5 Application; 4.5.1 Procedure to Do ECD; 4.5.2 ECD Application; 5.4.1 VCD Application; 4.5.3 UV Correction; References

Chapter 5 Vibrational Circular Dichroism and Raman Optical Activity5.1 Exciton Chirality; 5.2 Quantum Theory Basis; 5.2.1 VCD and IR; 5.2.2 ROA and Raman Scattering; 5.3 Principles Using VCD and ROA; 5.4 Application; 5.4.2 ROA Application; References; Chapter 6 Combinational Use of Different Methods; 6.1 Tactics to Select Methods; 6.1.1 13C NMR Methods; 6.1.2 OR and ORD; 6.1.3 Matrix; 6.1.4 ECD; 6.1.5 VCD Method; 6.2 Examples and Discussion; 6.3 Revised Structures; 6.3.1 ORD Method; 6.3.2 Combinational Use of OR and ECD; 6.3.3 VCD and ECD; 6.3.4 Comprehensive Use of OR, ECD, and VCD

ReferencesPart III Reactions; Chapter 7 Enantioselective Reaction; 7.1 Enantioselective Addition; 7.1.1 Organic Zn- or Zn-Ti Reagent; 7.1.2 Organic Cu-Zn, Cu-Li Reagent; 7.1.3 Organo-Fe Complexes; 7.1.4 Other Organo-Metallic Complexes; 7.1.5 Organo-Si Reagents; 7.2 Enantioselective Reduction; 7.2.1 Green Chemistry; 7.6.2 Auto-Self Catalysis; 7.3 Enantioselective Oxidation; 7.4 Prediction of ee Using Calculations; 7.5 Catalyst Types; 7.5.1 Amino Alcohols; 7.5.2 Chiral Ligands Containing N-O Group; 7.5.3 Chiral Axial Catalysts; 7.5.4 Solid-Supported Chiral Compounds

7.5.5 Spiral Chiral Compounds

Notes:

Description based upon print version of record.

Includes bibliographical references at the end of each chapters and index.

Description based on online resource; title from PDF title page (ebrary, viewed November 5, 2015).

ISBN:

9783527688173

352768817X

9783527688166

3527688161

OCLC:

908335774