Reactions and Syntheses E-Book

Lutz F. Tietze

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 1068

Veröffentlichungsjahr: 2015

Beschreibung

The second edition of this classic text book has been completely revised, updated, and extended to include chapters on biomimetic amination reactions, Wacker oxidation, and useful domino reactions.

The first-class author team with long-standing experience in practical courses on organic chemistry covers a multitude of preparative procedures of reaction types and compound classes indispensable in modern organic synthesis. Throughout, the experiments are accompanied by the theoretical and mechanistic fundamentals, while the clearly structured sub-chapters provide concise background information, retrosynthetic analysis, information on isolation and purification, analytical data as well as current literature citations. Finally, in each case the synthesis is labeled with one of three levels of difficulty.

An indispensable manual for students and lecturers in chemistry, organic chemists, as well as lab technicians and chemists in the pharmaceutical and agrochemical industries.

Leseprobe

Table of Contents

Cover

Related Titles

Title Page

Copyright

Preface to the First Edition

1 Background

2 Organization of the Book and Directions for Its Use

References

Preface to the Second Edition

Reference

Acknowledgments

About the Authors

Abbreviations and Symbols

Chapter 1: C–C Bond Formation

1.1 Nucleophilic Addition to Aldehydes, Ketones, Carboxylic Acid Derivatives (Esters, Anhydrides), and α,β-Unsaturated Carbonyl Compounds; Carbonyl Olefination

1.2 Alkylation of Aldehydes/Ketones, Carboxylic Acids, and β-Dicarbonyl Compounds

1.3 Reactions of the Aldol and Mannich Type

1.4 Electrophilic and Nucleophilic Acylation

1.5 Reactions of Alkenes Via Carbenium Ions

1.6 Transition-Metal-Catalyzed Reactions

1.7 Pericyclic Reactions

1.8 Radical Reactions

Chapter 2: Oxidation and Reduction

2.1 Epoxidation of C=C Bonds

2.2 Dihydroxylation of C=C Bonds

2.3 Oxidation of Alcohols to Carbonyl Compounds

2.4 Enantioselective Reduction of Ketones

2.5 Biomimetic Reductive Amination

2.6 Enantioselective Wacker Oxidation

Chapter 3: Heterocyclic Compounds

3.1 Three- and Four-Membered Heterocycles

3.2 Five-Membered Heterocycles

3.3 Six-Membered Heterocycles

3.4 Condensed Heterocycles

3.5 Other Heterocyclic Systems, Heterocyclic Dyes

Chapter 4: Selected Natural Products

4.1 Isoprenoids

4.2 Carbohydrates

4.3 Amino Acids and Peptides

4.4 Nucleotides and Oligonucleotides

Chapter 5: Domino Reactions

5.1 Domino Reactions in Synthetic Methodology

5.2 Domino Reactions in the Synthesis of Alkaloids

5.3 Domino Reactions in the Synthesis of Isoprenoids

5.4 Domino Reactions for the Synthesis of Chromans and Dioxins

5.5 Domino Reactions in the Synthesis of Chiroptical Switches

Index of Reactions

Index of Products

Subject Index

End User License Agreement

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Guide

Cover

Table of Contents

Preface to the First Edition

Begin Reading

List of Tables

Table 3.1

Table 3.2

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Lutz F. Tietze, Theophil Eicher, Ulf Diederichsen, Andreas Speicher, and Nina Schützenmeister

Reactions and Syntheses

In the Organic Chemistry Laboratory

Second, Completely Revised and Updated Edition

The Authors

Prof. Dr. Lutz F. Tietze

Georg-August-University Göttingen

Institute of Organic and Biomolecular Chemistry

Tammannstr. 2

37077 Göttingen

Germany

Prof. Dr. Theophil Eicher

Saarland University

Campus B6.1

66123 Saarbrücken

Germany

Prof. Dr. Ulf Diederichsen

Georg-August-University Göttingen

Institute of Organic and Biomolecular Chemistry

Tammannstr. 4

37077 Göttingen

Germany

Prof. Dr. Andreas Speicher

Saarland University

FR 8.1 - Organic Chemistry

Campus C4.2

66041 Saarbrücken

Germany

Dr. Nina Schützenmeister

University of Bristol

School of Chemistry

Cantock's Close

Bristol, BS8 1TS

UK

Cover

The cover image was kindly supplied by Professor Lutz F. Tietze.

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at <http://dnb.d-nb.de>.

© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany

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Print ISBN: 978-3-527-33814-6

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Preface to the First Edition

1 Background

The book Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium was first published in German in 1981, with a second edition in 1991, and was translated into Japanese in 1984 (second edition 1995), English in 1989, Chinese in 1999, Russian in 2000, and Korean in 2002. The intention was

to associate classes of compounds and functionalities with reaction types and mechanisms,

to offer a great number of reliable preparative procedures of general importance, and

to show the usefulness and robustness of the offered procedures for the synthesis of selected interesting compounds of relevance in biology, pharmacy, and medicine.

Since the last German edition, many new preparative procedures have been developed showing high chemo, regio, diastereo, and enantioselectivity, which frequently approach the selectivity of enzymatic transformations with the advantage of lower substrate specificity. In addition, new methods such as combinatorial chemistry, solid-phase chemistry, high-pressure chemistry, and the use of microwaves for heating have been introduced. Moreover, the efficiency of a synthesis, which can be defined as the increase in complexity per transformation, the avoidance of toxic reagents and solvents, and the preservation of resources are important issues in modern preparative organic chemistry. Significant developments in the last years have been realized in transition-metal catalysis, organocatalysis, and domino reactions. This progress has been impressively documented in Classics of Total Synthesis [1], Organic Synthesis Highlights [2], and Domino Reactions in Organic Synthesis [3].

As a consequence, we now present this book Reactions and Syntheses in the Organic Chemistry Laboratory in a new form with respect to its concept and organization and extensively renewed with respect to its content.

Its major highlights are as follows:

The basic units as well as the main objectives are

syntheses

(up to multistep syntheses with more than five steps) of interesting and instructive target molecules from various fields of organic chemistry. Each synthesis is centered around one or more methods and reaction principles of general synthetic relevance.

As before, the users of the new book are provided with carefully elaborated experiments, which are described in preparative and analytical detail. However, experiments and syntheses are accompanied throughout in concentrated form by the required general, theoretical, and mechanistic background and explanations. Special attention is given to retrosynthetic analysis and alternative approaches of synthesis for a given target molecule.

To allow the inclusion of a representative and qualified spectrum of contemporary synthetic methods, more than 70% of the content of the former book has been replaced by more recent and more relevant experimental examples. The remaining (older) syntheses have been “updated” with respect to description of their general background.

Considering the various types of users of the book in the past, there has been a definite and broad acceptance among chemists and pharmacists on a more advanced level, besides graduate students and researchers in universities and industry. From these considerations, the following consequences have emerged for the third edition:

General laboratory information, such as safety, first aid, performance of chemical reactions, instrumentation and standard apparatus, and isolation and purification of products, has been omitted. Methods for the formation and transformation of basic functional groups in organic compounds, regarded as important at the elementary education level in organic laboratory practice, are not described. These topics are comprehensively covered in other relevant textbooks [4–6].

The deletion of these elementary aspects of organic chemistry has allowed us to describe in more detail of the advanced synthetic methods and to include mechanistic aspects and to incorporate total syntheses and retrosynthetic analyses.

2 Organization of the Book and Directions for Its Use

The book is divided into four chapters with several sections:

Chapter

1

: C–C bond formation

Chapter

2

: Oxidation and reduction

Chapter

3

: Heterocyclic compounds

Chapter

4

: Selected natural products.

The sections (e.g., 1.1 and 1.2) contain procedures and syntheses (e.g., 1.1.1 and 1.1.2) as specified at the beginning of the section and in the Table of Contents (cf. p. II). Each synthesis is organized as follows:

In the general part (a), the

structural formula

of the target molecule and the

topics

of the presented synthesis (important for rapid information!) are given, which is followed by

introductory information

on the target molecule,

retrosynthesis

[7], and

planning of the synthesis

(possibilities, strategies, and synthetic alternatives; considerations on practicability for laboratory use).

In part (b), the

synthesis of the target molecule

and the

synthetic steps

performed in the experimental part are described. This is accompanied by information about the mechanism(s), the stereochemical outcome, and the selectivity of the transformations (specific reaction principles). Finally, the number of steps performed and the yields obtained are summarized. In general, Section (b) contains a complete

scheme of the synthesis

performed.

In Section (c), individual

experimental procedures

are described. Each procedure has the following structure:

An identification number, which characterizes the prepared compound according to chapter, section, and synthesis (e.g.,

1.1.1.1

and

1.1.1.2

); the identification number carries one or more asterisks (*, **, ***) according to the degree of difficulty of the procedure.

Literature reference(s) for the prepared compound.

A formula equation, which gives structures of reactants and products, and their relative molecular masses. In general, apparatus is not discussed in detail; however, in special cases, information about specialized equipment (photochemical, high-pressure, microwave, etc.) is given.

Throughout, the procedures are presented in two parts. The first, describing the reaction, often includes additional notes about purification and characteristics of the substrates, such as toxicity and safety aspects. The second describes the work-up, isolation, and purification of the product, along with criteria of purity (mp, bp, n

D

, TLC/

R

f

, [α]

D

), notes about characteristics of the product, and other crucial experimental details.

Characterization of the product by spectral data (IR, UV–vis,

1

H and

13

C NMR, MS). In selected cases, the preparation of derivatives together with their instrumental and chemical analysis is given.

The presentation of each synthesis is concluded by a compilation of the

literature references

cited in Sections (a–c). They cover the primary literature on the synthesis, its steps, and its topics, and refer to important collective articles, reviews, and textbooks of advanced organic chemistry [8].

References

1. (a) Nicolaou, K.C. and Sorensen, E.J. (1997)

Classics in Total Synthesis

, Wiley-VCH Verlag GmbH, Weinheim;(b) Nicolaou, K.C. and Snyder, S.A. (2003)

Classics in Total Synthesis II

, Wiley-VCH Verlag GmbH, Weinheim.

2. Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K., Reissig, H.-U., Waldmann, H., Schmalz, H.-G., and Wirth, Th. (eds) (1991-2003)

Organic Synthesis Highlights I–V

, Wiley-VCH Verlag GmbH, Weinheim.

3. Tietze, L.F., Brasche, G., and Gericke, K.M. (2006)

Domino Reactions in Organic Synthesis

, Wiley-VCH Verlag GmbH, Weinheim.

4. (2001)

Organikum

, 21st edn, Wiley-VCH Verlag GmbH, Weinheim.

5. Hünig, S., Kreitmeier, P., Märkl, G., and Sauer, J. (2007)

Arbeitsmethoden in der Organischen Chemie (mit Einführungs-praktikum)

, 2nd edn, Verlag Lehmanns, Berlin.

6. Larock, R.C. (1999)

Comprehensive Organic Transformations (A Guide to Functional Group Preparations)

, 2nd edn, Wiley-VCH Verlag GmbH, Weinheim.

7. (a) Retrosynthesis is oriented toward the concepts and terminology of Warren, S. (1982)

Organic Synthesis – The Disconnection Approach

, John Wiley & Sons, Inc., New York;(b) Warren, S. (1978)

Designing Organic Syntheses

, John Wiley & Sons, Inc., New York;(c) Corey, E.J. and Cheng, X.-M. (1989)

The Logic of Chemical Synthesis

, John Wiley & Sons, Inc., New York.

8. For example (a) Smith, M.B. (2013)

March's Advanced Organic Chemistry

, 7th edn, John Wiley & Sons, Inc., Hoboken, NJ;(b) Carey, F.A. and Sundberg, R.J. (1995)

Organische Chemie

, Wiley-VCH Verlag GmbH, Weinheim;(c) Quinkert, G., Egert, E., and Griesinger, C. (1995)

Aspekte der Organischen Chemie

, Wiley-VCH Verlag GmbH, Weinheim;(d) Brückner, R. (2004)

Reaktionsmechanismen (Organische Reaktionen, Stereochemie, moderne Synthesemethoden)

, 3rd edn, Spektrum Akademischer Verlag, Heidelberg;(e) Eliel, E.L., Wilen, S.H., and Doyle, M.P. (2001)

Basic Organic Stereochemistry

, John Wiley & Sons, Inc., New York;(f) Fuhrhop, J.-H. and Li, G. (2003)

Organic Synthesis

, 3rd edn, Wiley-VCH Verlag GmbH, Weinheim;(g) Kocieński, P.J. (2005)

Protecting Groups

, 3rd edn, Georg Thieme Verlag, Stuttgart;(h) Helmchen, G., Hoffmann, R.W., Mulzer, J., and Schaumann, E. (1996)

Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis

, 4th edn, vol. E21, Georg Thieme Verlag, Stuttgart;(i) Hauptmann, S. and Mann, G. (1996)

Stereochemie

, Spektrum Akademischer Verlag, Heidelberg.

Preface to the Second Edition

Since the appearance of the first edition of the book Reaction and Syntheses in 2007, new facets in synthesis have arisen. The synthesis of chemical compounds is still a key issue in chemistry not only in academia but also in industry, but besides the chemo, region, diastereo, and enantioselectivity, new aspects in synthesis have gained importance: efficiency, reduction of waste, conservation of our resources, protecting of our environment, and finally also economic advantages by reducing the transformation time and the amount of the needed chemicals. Therefore, we have added a fifth chapter, which deals with domino reactions to meet all these requirements. A domino reaction is defined as a process of two or more bond-forming reactions under identical reaction conditions, in which the latter transformations take place on the functionalities obtained in the former bond-forming reactions [1]. In the process, one, two, three, and more substrates can be involved. Thus, multicomponent transformations are domino reactions per definition. The quality and the usefulness of domino reactions are related to the increase in complexity and diversity in the final product compared to the starting material.

In addition, besides the Heck, the Suzuki–Miyaura, and Songashira reactions, we have also added novel transition-metal-catalyzed reactions such as the alkene as well as the alkyne ring-closing metathesis and an enantioselective Wacker oxidation; furthermore, novel Ru catalysts are prepared, and organocatalytic reactions have been introduced. Moreover, examples of CH activation in organic synthesis are included and also novel interesting classes of new materials as molecular switches.

Finally, some procedures, which did not meet our expectations in reproducibility, have been removed or modified.

On the other hand, we did not change the concept with the retrosynthetic analysis of the products and discussing the mechanism of the different steps, because this approach has been highly successful and proven its value.

Reference

1. (a) Tietze, L.F. (1996)

Chem. Rev.

,

96

, 115–136;(b) Tietze, L.F., Brasche, G., and Gericke, K.M. (2006)

Domino Reactions in Organic Synthesis

, Wiley-VCH Verlag GmbH, Weinheim;(c) Tietze, L.F. (ed.) (2014)

Domino Reactions – Concepts for Efficient Organic Synthesis

, Wiley-VCH Verlag GmbH, Weinheim.

Acknowledgments

We are indebted, above all, to the collaborators of the groups in Göttingen and Saarbrücken of Lutz F. Tietze, Ulf Diederichsen, and Andreas Speicher, who performed the laboratory work for testing the suitability of the selected synthetic examples.

L.F.T. is especially indebted to Mrs Katja Grube for improving a few of the procedures and to Mrs Martina Pretor for her help in updating the literature.

We are also thankful to the Fonds der Chemischen Industrie for generous financial support.

Furthermore, we are grateful to Prof. Dr. Alois Fürstner, MPI für Kohleforschung, Mülheim; Prof. Dr. Markus Rueping, Institute of Organic Chemistry, RWTH-Aachen; Prof. Dr. U. Kazmaier, Institute of Organic Chemistry, University of the Saarland; Prof. Dr. P. Knochel, Institute of Organic Chemistry Ludwig-Maximilians University, München; Prof. Dr. J. A. Wisner, University of Western Ontario, London Ontario, Canada; and Dr. L. Kattner, Fa. Endotherm, Saarbrücken, for making available experimental procedures from their research field, and to Prof. Dr. R. Schmidt for helpful suggestions. We are also very thankful to the staff of the editorial office of Wiley-VCH for their efficient assistance and cooperation.

Göttingen and Saarbrücken, Germany Summer 2014

Lutz F. TietzeTheophil EicherUlf DiederichsenAndreas SpeicherNina Schützenmeister

About the Authors

Lutz F. Tietze obtained his Ph.D. in 1968 in Kiel. He then worked as a research associate with Prof. G. Büchi at MIT, Cambridge, USA, as well as with Prof. A. Battersby in Cambridge, UK. Since 1978 he has been Professor and Head of the Institute of Organic and Biomolecular Chemistry at the Georg-August-University in Göttingen. His research focuses on the development of efficient synthetic methods as domino reactions, the total synthesis of natural products, and the design of new selective anticancer agents. Professor Tietze has received many prizes, inter alia the highly prestigious Emil Fischer Medal of the GDCh. He was speaker of a Sonderforschungsbereich, delegate of the DFG Fachkollegium and obtained several guest professorships. He is member of the Göttingen Academy of Sciences and Humanities, Dr. h.c. of the University of Szeged, Chairman of the DZfCh, member of the DHKZ, and has been awarded in 2012 with the position of a Distinguished Research Professor. He has over 460 papers, 34 patents and five books to his name.

Theophil Eicher studied chemistry at the University of Heidelberg, Germany, and obtained his Ph.D. under Georg Wittig in 1960. After postdoctoral work at Columbia University, New York, USA, in the laboratories of Ronald Breslow, he habilitated 1967 at the University of Würzburg, Germany, under Siegfried Hünig. In 1974 he was appointed as Associate Professor at the University of Hamburg, Germany, in 1976 as Full Professor of Organic Chemistry at the University of Dortmund, Germany. Since 1982, he worked as Full Professor at Saarland University, Germany, and was retired in 2000. His research interests concerned the synthetic chemistry of cyclopropenones and triafulvenes, as well as natural product synthesis in the field of bryophyte constituents. He is co-author of several books. Jointly with L. F. Tietze, he was awarded the literature prize of the ``Fonds der chemischen Industrie''. He is Dr. h. c. and Prof. a. h. of the Facultad de Quimica of the Universidad de la Republica, Montevideo/Uruguay.

Ulf Diederichsenstudied Chemistry in Freiburg, Germany, with a diploma work in organic synthesis and completed his Ph.D. in 1993 under the supervision of Albert Eschenmoser at the ETH Zürich working on homo- and glucose-DNA. After postdoctoral work on radical chemistry at the University of Pittsburgh, USA, in the group of Dennis Curran, he gained his habilitation at the Technical University Munich, Germany. In 1999, he was appointed professor of Organic Chemistry at the University Würzburg, Germany, until joining the Georg-August-University in Göttingen, Germany, in 2001 as full professor of Organic Chemistry. He was visiting professor at the LMU Munich and Goering Visiting Professor at the University of Wisconsin, USA. He got the Karl Winnacker stipend and Hellmut-Bredereck award and is member of Göttingen Academy of Sciences and Humanities.

Andreas Speicher studied chemistry at Saarland University, Germany. He obtained his Ph.D. in 1994 under Theophil Eicher and was honored with the Eduard- Martin-Award of his university. He started his independent scientific career and completed habilitation in 2003. He is head of a research group and university lecturer for organic chemistry at the Saarland University and was appointed extraordinary professor in 2011. He is temporarily holding a guest professorship at the University of Strasbourg/France since 2006 and is co-author of several books. His research interests are directed to synthesis and characterization of chemically and biologically relevant natural products, especially to axially chiral macrocyclic compounds.

Nina Schützenmeister studied chemistry at the Georg-August-University in Göttingen. After finishing her diploma thesis at the ETH Zürich in the group of Peter H. Seeberger she completed her Ph.D. in 2012 under supervision of Lutz F. Tietze at the Georg-August-University in Göttingen. She then worked as a postdoctoral fellow with Christian Griesinger at the Max-Planck-Institute for Biophysical Chemistry in Göttingen and is currently a Marie-Curie fellow in the group of Varinder K. Aggarwal F.R.S. at the University of Bristol, United Kingdom.