One approach to organic synthesis is retrosynthetic analysis. With
this approach chemists start with the structures of their target
molecules and progressively cut bonds to create simpler molecules.
Reversing this process gives a synthetic route to the target
molecule from simpler starting materials. This
‚disconnection‘ approach to synthesis is now a
fundamental part of every organic synthesis course.
Workbook for Organic Synthesis: The Disconnection Approach,
2nd Edition
This workbook provides a comprehensive graded set of problems to
illustrate and develop the themes of each of the chapters in the
textbook Organic Synthesis: The Disconnection Approach,
2nd Edition. Each problem is followed by a fully
explained solution and discussion. The examples extend the
student’s experience of the types of molecules being
synthesised by organic chemists, and the strategies they employ to
control their syntheses. By working through these examples students
will develop their skills in analysing synthetic challenges, and
build a toolkit of strategies for planning new syntheses. Examples
are drawn from pharmaceuticals, agrochemicals, natural products,
pheromones, perfumery and flavouring compounds, dyestuffs,
monomers, and intermediates used in more advanced synthetic work.
Reasons for wishing to synthesise each compound are given. Together
the workbook and textbook provide a complete course in
retrosynthetic analysis.
Organic Synthesis: The Disconnection Approach, 2nd
Edition
There are forty chapters in Organic Synthesis: The
Disconnection Approach, 2nd Edition: those on the
synthesis of given types of molecules alternate with strategy
chapters in which the methods just learnt are placed in a wider
context. The synthesis chapters cover many ways of making each type
of molecule starting with simple aromatic and aliphatic compounds
with one functional group and progressing to molecules with many
functional groups. The strategy chapters cover questions of
selectivity, protection, stereochemistry, and develop more advanced
thinking via reagents specifically designed for difficult problems.
In its second edition updated examples and techniques are included
and illustrated additional material has been added to take the
student to the level required by the sequel, Organic Synthesis:
Strategy and Control. Several chapters contain extensive new
material based on courses that the authors give to chemists in the
pharmaceutical industry.
Workbook for Organic Synthesis: The Disconnection Approach,
2nd edition, combined with the main textbook,
provides a full course in retrosynthetic analysis for chemistry and
biochemistry students, and a refresher course for organic chemists
working in industry and academia.
Inhaltsverzeichnis
Preface vii
General References ix
1. The Disconnection Approach 1
2. Basic Principles: Synthons and Reagents: Synthesis of
Aromatic Compounds 5
3. Strategy I: The Order of Events 11
4. One-Group C-X Disconnections 15
5. Strategy II: Chemoselectivity 21
6. Two-Group C-X Disconnections 29
7. Strategy III: Reversal of Polarity, Cyclisations, Summary of
Strategy 35
8. Amine Synthesis 41
9. Strategy IV: Protecting Groups 49
10. One-Group C-C Disconnections I: Alcohols 55
11. General Strategy A: Choosing a Disconnection 61
12. Strategy V: Stereoselectivity A 67
13. One-Group C-C Disconnections II: Carbonyl Compounds
75
14. Strategy VI: Regioselectivity 81
15. Alkene Synthesis 87
16. Strategy VII: Use of Acetylenes (Alkynes) 93
17. Two-Group C-C Disconnections I: Diels-Alder Reactions
99
18. Strategy VIII: Introduction to Carbonyl Condensations
105
19. Two-Group C-C Disconnections II: 1, 3-Difunctionalised
Compounds 111
20. Strategy IX: Control in Carbonyl Condensations 115
21. Two-Group C-C Disconnections III: 1, 5-Difunctionalised
Compounds Conjugate (Michael) Addition and Robinson Annelation
123
22. Strategy X: Aliphatic Nitro Compounds in Synthesis 129
23. Two-Group Disconnections IV: 1, 2-Difunctionalised Compounds
133
24. Strategy XI: Radical Reactions in Synthesis 139
25. Two-Group Disconnections V: 1, 4-Difunctionalised Compounds
147
26. Strategy XII: Reconnection 153
27. Two-Group C-C Disconnections VI: 1, 6-di Carbonyl
Compounds 159
28. General Strategy B: Strategy of Carbonyl Disconnections
165
29. Strategy XIII: Introduction to Ring Synthesis: Saturated
Heterocycles 173
30. Three-Membered Rings 181
31. Strategy XIV: Rearrangements in Synthesis 189
32. Four-Membered Rings: Photochemistry in Synthesis 195
33. Strategy XV: The Use of Ketenes in Synthesis 201
34. Five-Membered Rings 207
35. Strategy XVI: Pericyclic Reactions in Synthesis: Special
Methods for Five-Membered Rings 213
36. Six-Membered Rings 221
37. General Strategy C: Strategy of Ring Synthesis 227
38. Strategy XVII: Stereoselectivity B 235
39. Aromatic Heterocycles 245
40. General Strategy D: Advanced Strategy 255
Index 263
Über den Autor
Dr Stuart Warren Department of Chemistry, University of Cambridge, UK
Dr Warren is the author of the bestselling textbooks ‚Organic Synthesis: The Disconnection Approach‘ (Wiley), ‚Organic Synthesis: Strategy and Control‘ (Wiley) and ‚Organic Chemistry‘ (OUP)
Dr Paul Wyatt
School of Chemistry, University of Bristol, UK.
Dr Wyatt is Director of Undergraduate Studies for the School of Chemistry at Bristol University and also Director of BRISTOL Chem Lab S – a HEFCE Centre for Excellence in Teaching & Learning.?He is co-author, with Warren, of ‚Organic Synthesis: Strategy and Control‘
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