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Catalysis in Asymmetric Synthesis Postgraduate
Chemistry Series 2nd Edition Vittorio Caprio Digital
Instant Download
Author(s): Vittorio Caprio, Jonathan Williams
ISBN(s): 1405175192
Edition: 2nd
File Details: PDF, 4.55 MB
Year: 2009
Language: english
Catalysis in Asymmetric Synthesis
Second Edition
Postgraduate Chemistry Series
A series designed to provide a broad understanding of selected growth areas of
chemistry at postgraduate student and research level. Volumes concentrate on
material in advance of a normal undergraduate text, although the relevant back-
ground to a subject is included. Key discoveries and trends in current research are
highlighted, and volumes are extensively referenced and cross-referenced. Detailed
and effective indexes are an important feature of the series. In some universities,
the series will also serve as a valuable reference for final year honours students.

Editorial Board
Professor James Coxon (Editor-in-Chief), Department of Chemistry, University
of Canterbury, New Zealand.
Professor Pat Bailey, Department of Chemistry, University of Manchester, UK.
Professor Les Field, School of Chemistry, University of New South Wales, Sydney,
Australia.
Professor Dr. John Gladysz, Institut für Organische Chemie, Universität Erlangen-
Nürnberg, Germany.
Professor Philip Parsons, School of Chemistry, Physics and Environmental Sci-
ence, University of Sussex, UK.
Professor Peter Stang, Department of Chemistry, University of Utah, Utah, USA.

Titles in the Series

Protecting Groups in Organic Synthesis
James R. Hanson
Organic Synthesis with Carbohydrates
Geert-Jan Boons and Karl J. Hale
Organic Synthesis using Transition Metals
Roderick Bates
Stoichiometric Asymmetric Synthesis
Mark Rizzacasa and Michael Perkins
Catalysis in Asymmetric Synthesis (Second Edition)
Vittorio Caprio and Jonathan M. J. Williams
Reaction Mechanisms in Organic Synthesis
Rakesh Kumar Parashar

Forthcoming
Photochemistry of Organic Compounds: From Concepts to Practice
Petr Klán and Jakob Wirz
Practical Biotransformations
Gideon Grogan
Catalysis in Asymmetric Synthesis
Second Edition

Vittorio Caprio
Department of Chemistry
University of Auckland, Auckland, New Zealand
and

Jonathan M. J. Williams
Department of Chemistry
University of Bath, Bath, UK

A John Wiley and Sons, Ltd., Publication

This edition first published 2009


C Vittorio Caprio and Jonathan M.J. Williams

This text is based on “Catalysis in Asymmetric Synthesis” by Jonathan M.J. Williams, published by
Sheffield Academic Press in 1999 and acquired by Blackwell Publishing in 2002.

Blackwell Publishing was acquired by John Wiley & Sons in February 2007. Blackwell’s publishing
programme has been merged with Wiley’s global Scientific, Technical, and Medical business to form
Wiley-Blackwell.

Registered office
John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ,
United Kingdom

Editorial offices
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2121 State Avenue, Ames, Iowa 50014-8300, USA

For details of our global editorial offices, for customer services and for information about how
to apply for permission to reuse the copyright material in this book please see our website at
www.wiley.com/wiley-blackwell.

The right of the author to be identified as the author of this work has been asserted in accordance with
the Copyright, Designs and Patents Act 1988.

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system,
or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or
otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior
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brand names and product names used in this book are trade names, service marks, trademarks or
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is not engaged in rendering professional services. If professional advice or other expert assistance is
required, the services of a competent professional should be sought.

Library of Congress Cataloging-in-Publication Data

Caprio, Vittorio.
Catalysis in asymmetric synthesis / Vittorio Caprio and Jonathan M.J. Williams. – 2nd ed.
p. cm.
Includes bibliographical references and index.
ISBN 978-1-4051-9091-6 (cloth) – ISBN 978-1-4051-7519-7 (pbk. : alk. paper)
1. Asymmetric synthesis. 2. Catalysis. I. Williams, Jonathan M. J. II. Title.
QD262.C28 2008
541 .39–dc22 2008045023

A catalogue record for this book is available from the British Library.
Set in 10/12 pt Minion by Aptara Inc., New Delhi, India
Printed and bound in Great Britain by TJ International, Ltd, Padstow, Cornwall
1 2008
To Jenny
Contents

Preface to the Second Edition xi

Preface to the First Edition xiii

1 Introduction 1
1.1 Reactions Amenable to Asymmetric Catalysis 1
1.2 Assignment of (R) and (S) Stereochemical Descriptors 2
Futher Reading 6
References 7

2 Reduction of Alkenes 9
2.1 Asymmetric Hydrogenation with Rhodium Complexes 9
2.2 Asymmetric Hydrogenation with Ruthenium Catalysts 18
2.3 Alkene Hydrogenation with Titanium and
Zirconium Catalysts 24
2.4 Alkene Hydrogenation with Iridium Catalysts 25
2.5 Alkene Hydrogenation with Organocatalysts 28
2.6 Alkene Hydrosilylation 29
2.7 Alkene Hydroboration 32
2.8 Hydroamination 34
2.9 Hydroformylation 36
2.10 Hydroacylation of Alkenes 39
2.11 Hydrocyanation of Alkenes 40
References 40

3 Reduction of Ketones and Imines 47

3.1 Hydrogenation of Ketones 47
3.2 Hydrogenation and Transfer Hydrogenation of Imines
and Related Compounds 53
3.3 Transfer Hydrogenation of Ketones 56
3.4 Heterogeneous Hydrogenation 59
3.5 Reduction of Ketones Using Enantioselective
Borohydride Reagents 63
3.6 Hydrosilylation of Ketones 68
3.7 Hydrosilylation of Imines and Nitrones 73
References 75

vii
viii Contents

4 Epoxidation 81
4.1 Epoxidation of Allylic Alcohols 81
4.2 Epoxidation with Metal(salen) Complexes 88
4.3 Epoxidation Using Metal–Porphyrin-Based Catalysts 94
4.4 Other Metal-Catalysed Epoxidations of
Unfunctionalised Olefins 95
4.5 Epoxidation of Electron-Deficient Alkenes 96
4.6 Epoxidation with Iminium Salts 101
4.7 Epoxidation with Ketone Catalysts 102
4.8 Epoxidation of Aldehydes 105
4.9 Aziridination of Alkenes 106
4.10 Aziridination of Imines 108
References 109

5 Further Oxidation Reactions 117

5.1 Dihydroxylation 117
5.2 Aminohydroxylation 126
5.3 α-Heterofunctionalisation of Aldehydes and Ketones 130
5.4 Oxidation of C–H 136
5.5 Baeyer–Villiger Oxidation 138
5.6 Oxidation of Sulfides 139
References 142

6 Nucleophilic Addition to Carbonyl Compounds 147

6.1 Addition of Organozincs to Carbonyl Compounds 147
6.2 Addition of Cyanide to Aldehydes and Ketones 153
6.3 Allylation of Aldehydes 160
6.4 Hydrophosphonylation of Aldehydes 165
6.5 Nucleophilic Additions to Imines 166
References 173

7 The Aldol and Related Reactions 179

7.1 The Aldol Reaction 180
7.2 Isocyanide and Related Aldol Reactions 191
7.3 The Nitroaldol Reaction 193
7.4 Addition of Enolates to Imines 195
7.5 Darzens Condensation 200
7.6 Morita–Baylis–Hillman Reaction 201
7.7 Carbonyl-Ene Reactions 203
References 208

8 Cycloadditions 213
8.1 Diels–Alder Reactions 213
8.2 Inverse Electron Demand Diels–Alder Reactions 231
 Contents ix

8.3 Hetero-Diels–Alder Reactions 232

8.4 1,3-Dipolar Cycloaddition Reactions 240
8.5 [2+2] Cycloadditions 246
8.6 Pauson–Khand-Type Reactions 249
References 251

9 Catalytic Reactions Involving Carbenes and Ylides 257

9.1 Cyclopropanation 257
9.2 Insertion Reactions 268
9.3 Asymmetric Ylide Reactions 273
References 275

10 Catalytic Carbon–Carbon Bond-Forming Reactions 281

10.1 Cross-Coupling Reactions 282
10.2 Metal-Catalysed Allylic Substitution 284
10.3 Heck Reactions 296
10.4 Alkylmetalation of Alkenes 302
References 305

11 Conjugate Addition Reactions 311

11.1 Conjugate Addition of Enolates 311
11.2 Conjugate Addition of Sulfur Nucleophiles 317
11.3 Conjugate Addition of Nonstabilised Nucleophiles 320
11.4 Conjugate Addition with Nitrogen-Based Nucleophiles
and Electrophiles 325
References 328

12 Further Catalytic Reactions 333

12.1 Isomerisations and Rearrangements 333
12.2 Deprotonation Reactions 336
12.3 Protonation Reactions 336
12.4 Alkylation and Allylation of Enolates 338
12.5 Formation of Alkenes 342
12.6 Oxyselenylation-Elimination Reactions 344
12.7 The Benzoin Condensation 344
12.8 Ester Formation and Hydrolysis 345
12.9 Ring-Opening of Epoxides 349
References 355

Index 361
Preface to the Second Edition

Since publication of the first edition of this book in 1998 the area of asymmetric
catalysis has grown apace. Major advances in organo- and bifunctional catalysis
have occurred in this millennium. Thus, the release of a second, updated edition
is timely.
The book aims to capture the material published up to the present. As in the first
edition the emphasis is on nonenzymatic methods although references to reviews
on catalysis with enzymes are included.
We have strived to include as many examples of catalysts and their scope as
possible within the confines of a book of this size, while maintaining readability of
this text and its use as a teaching aid. Further coverage of specific catalysts can be
obtained from the many comprehensive reviews referenced.
We are grateful to Amanda Heapy for all her helpful feedback and to Dr Jenny
Gibson for proof reading and editorial assistance.

V. Caprio
University of Auckland

J. M. J. Williams
University of Bath

xi
Preface to the First Edition

Asymmetric synthesis has become a major aspect of modern organic chemistry.

The importance of stereochemical purity in pharmaceutical products has been one
driving force in the quest for improved control over the stereochemical output of
organic reactions. The fact is, like it or not, stereochemistry is hard to avoid.
Asymmetric catalysis is a very important aspect of asymmetric synthesis, and one
that has seen tremendous activity during the 1990s. This book aims to capture the
latest results in asymmetric catalysis, and covers the literature up until June/July
1998. A few references as late as October 1998 have also been included. The
emphasis in this book has been on nonenzymatic methods for asymmetric catalysis,
although key references to enzyme-catalysed reactions have been incorporated
where appropriate.
It cannot be possible to be comprehensive in a book of this size, although
hopefully there are no major omissions. I apologise if I have omitted any ‘favourite’
reactions, or if a topic has not been treated with the depth that it may deserve.
The emphasis, in general, has been on asymmetric catalytic reactions which are as
current as possible.
I am grateful to my former mentors, Professor S. G. Davies (Oxford) and
Professor D. A. Evans (Harvard), who introduced me to asymmetric synthesis and
asymmetric catalysis. I am also indebted to my current coworkers and students
who help to keep organic chemistry alive for me with their enthusiasm for the
subject.
My thanks also go to Mrs J. W. Curtis, who has typed the bulk of the manuscript,
and Miss H. L. Haughton, who helped with many of the chemical structures.
Finally, I am especially grateful to my wife, Cathy, who has not complained
about the extra time I have needed to work during the preparation of this book.

J. M. J. Williams
University of Bath

xiii
Chapter 1
Introduction

There are several ways of producing compounds as single enantiomers. The res-
olution of a mixture of enantiomers can often be the cheapest, most practical
way of obtaining enantiomerically pure material. The conversion of a cheap enan-
tiomerically pure starting material into another derivative represents another useful
technique in some cases.
However, asymmetric synthesis can provide a more general approach to the
preparation of enantiomerically enriched compounds. Asymmetric synthesis is
limited by the range and scope of available methodology. Fortunately, with so
much research in the area, there are many methods now available, with further
asymmetric reactions being developed each year. There may still be cases where
asymmetric synthesis doesn’t provide the best method for the preparation of a par-
ticular enantiomerically pure compound, but it certainly allows for the preparation
of a more diverse range of structures.
Asymmetric catalysis is an especially appealing aspect of asymmetric synthesis.
Small amounts of a catalyst (frequently less than 1 mol%) can be used to control
the stereochemistry of the bulk reaction. The use of a catalyst often makes the
isolation of a product easier, since there is less unwanted material to remove at the
end of a reaction.

1.1 Reactions Amenable to Asymmetric Catalysis

From a synthetic viewpoint, the individual chapter titles in the book give a fair
impression of the scope of synthetic processes involved. The types of reaction
amenable to asymmetric catalysis can also be considered from a more stereochem-
ical viewpoint.
Most reactions involving asymmetric catalysis are based around the conversion
of a planar sp2 carbon atom into a tetrahedral sp3 carbon atom. This category of
reactions includes asymmetric hydrogenation of alkenes and ketones, as well as the
addition of other reagents to these groups as identified in Figure 1.1.
Substrates containing enantiotopic groups can be converted into enantiomeri-
cally enriched compounds using asymmetric catalysis with representative examples

Catalysis in Asymmetric Synthesis 2e

C 2009 Vittorio Caprio and Jonathan M.J. Williams

1
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Unit 1: Assessment criteria and rubrics

Learning Objective 1: Key terms and definitions
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 1: Diagram/Chart/Graph]
Learning Objective 2: Ethical considerations and implications
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
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• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Learning Objective 4: Current trends and future directions
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Learning Objective 5: Literature review and discussion
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Ethical considerations and implications
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Note: Practical applications and examples
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 7: Case studies and real-world applications
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 8: Diagram/Chart/Graph]
Example 8: Theoretical framework and methodology
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Critical analysis and evaluation
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
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Note: Theoretical framework and methodology
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 11: Diagram/Chart/Graph]
Important: Assessment criteria and rubrics
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Critical analysis and evaluation
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Theoretical framework and methodology
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Assessment criteria and rubrics
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Research findings and conclusions
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Ethical considerations and implications
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Statistical analysis and interpretation
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Fundamental concepts and principles
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 19: Interdisciplinary approaches
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Test 3: Interdisciplinary approaches
Note: Statistical analysis and interpretation
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 21: Diagram/Chart/Graph]
Note: Study tips and learning strategies
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Critical analysis and evaluation
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 23: Diagram/Chart/Graph]
Example 23: Statistical analysis and interpretation
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 24: Diagram/Chart/Graph]
Key Concept: Comparative analysis and synthesis
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Problem-solving strategies and techniques
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Comparative analysis and synthesis
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Interdisciplinary approaches
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Critical analysis and evaluation
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Historical development and evolution
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Introduction 4: Case studies and real-world applications
Example 30: Assessment criteria and rubrics
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 31: Diagram/Chart/Graph]
Definition: Practical applications and examples
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Definition: Fundamental concepts and principles
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Historical development and evolution
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Critical analysis and evaluation
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Comparative analysis and synthesis
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Ethical considerations and implications
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Literature review and discussion
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Note: Experimental procedures and results
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 39: Diagram/Chart/Graph]
Practice Problem 39: Historical development and evolution
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Review 5: Literature review and discussion
Important: Statistical analysis and interpretation
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 41: Diagram/Chart/Graph]
Practice Problem 41: Key terms and definitions
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 42: Theoretical framework and methodology
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 43: Diagram/Chart/Graph]
Remember: Historical development and evolution
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Literature review and discussion
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Practical applications and examples
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Best practices and recommendations
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 47: Case studies and real-world applications
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 48: Experimental procedures and results
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 49: Study tips and learning strategies
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Methodology 6: Current trends and future directions
Practice Problem 50: Problem-solving strategies and techniques
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 51: Diagram/Chart/Graph]
Remember: Literature review and discussion
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- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 52: Study tips and learning strategies
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Important: Assessment criteria and rubrics
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 54: Diagram/Chart/Graph]
Note: Historical development and evolution
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 55: Diagram/Chart/Graph]
Note: Literature review and discussion
• Key terms and definitions
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- Note: Important consideration
Note: Research findings and conclusions
• Experimental procedures and results
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- Example: Practical application scenario
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Note: Literature review and discussion
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- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
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[Figure 59: Diagram/Chart/Graph]
Important: Literature review and discussion
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Abstract 7: Comparative analysis and synthesis
Practice Problem 60: Problem-solving strategies and techniques
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Best practices and recommendations
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 62: Diagram/Chart/Graph]
Important: Research findings and conclusions
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Learning outcomes and objectives
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 64: Diagram/Chart/Graph]
Key Concept: Ethical considerations and implications
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Problem-solving strategies and techniques
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 66: Diagram/Chart/Graph]
Practice Problem 66: Problem-solving strategies and techniques
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Practical applications and examples
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Remember: Ethical considerations and implications
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
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