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Workbook for Organic Synthesis. Strategy and Control. Edition No. 1

  • ID: 5227466
  • Book
  • April 2008
  • 502 Pages
  • John Wiley and Sons Ltd
Workbook for Organic Synthesis: Strategy and Control

Paul Wyatt

Senior Lecturer and Director of Undergraduate Studies, School of Chemistry, University of Bristol, UK

Stuart Warren

Reader in Organic Chemistry, Department of Chemistry, University of Cambridge, UK.

Workbook for Organic Synthesis: Strategy and Control
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: Strategy and Control. 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. Together the workbook and textbook provide a complete course in advanced organic synthesis.

Organic Synthesis: Strategy and Control
Organic Synthesis: Strategy and Control is a sequel to Stuart Warren's bestseller Organic Synthesis: The Disconnection Approach. The 'Disconnection' book concentrated on the planning behind the synthesis of compounds. This book focuses on putting the planning into practice. The two themes of the book are strategy and control: solving problems either by finding an alternative strategy or by controlling any established strategy to make it work.

The book is divided into five sections that deal with selectivity, carbon-carbon single bonds, carbon-carbon double bonds, stereochemistry and functional group strategy. Interpenetrating this structure, the 36 chapters start with classic methods and progress to modern methods and modern strategic considerations. Heterocyclic chemistry is treated throughout the book with full mechanistic explanations as part of organic chemistry rather than a separate entity.

Students and professional chemists familiar with Organic Synthesis: The Disconnection Approach will enjoy the leap into a book designed for chemists at the coalface of organic synthesis.
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A. Introduction: Selectivity.

1. Planning Organic Syntheses: Tactics, Strategy and Control.

2. Chemoselectivity.

3. Regioselectivity: Controlled Aldol Reactions.

4. Stereoselectivity: Stereoselective Aldol Reactions.

5. Alternative Strategies for Enone Synthesis.

6. Choosing a Strategy: The Synthesis of Cyclopentenones.

B. Making Carbon-Carbon Bonds.

7. The Ortho Strategy for Aromatic Compounds.

8. -complexes of Metals.

9. Controlling the Michael Reaction.

10. Specific Enol Equivalents.

12. Allyl Anions.

13. Homoenolates.

14. Acyl Anion Equivalents.

C. Carbon-Carbon Double Bonds.

15. Synthesis of Double Bonds of Defined Stereochemistry.

16. Vinyl Anions.

17. Electrophilic Attack on Alkenes.

18. Vinyl Cations.

19. Allyl Alcohols: Allyl Cation Equivalents (and More).

D. Stereochemistry.

20. Control of Stereochemistry -

21. Diastereoselectivity.

22. Resolution.

23. The Chiral Pool: Asymmetric Synthesis with Natural Products as Starting Materials.

24. Asymmetric Induction I: Reagent-Based Strategy.

25. Asymmetric Induction II: Asymmetric Catalysis: Formation of C-O and C-N Bonds.

26. Asymmetric Induction III: Asymmetric Catalysis: Formation of C-H and C-C Bonds.

27. Asymmetric Induction IV: Substrate-Based Strategy.

28. Kinetic Resolution.

29. Enzymes: biological Methods in Asymmetric Synthesis.

30. New Chiral Centres from Old: Enantiomerically Pure Compounds and Sophisticated Syntheses.

31. Strategy of Asymmetric Synthesis.

E. Functional Group Strategy.

32. Functionalisation of Pyridine.

33. Oxidation of Aromatic Rings and of Enol(ate)s.

34. Functionality and Pericyclic Reactions: Nitrogen Heterocycles by Cycloadditions and Sigmatropic Rearrangements.

35. Synthesis and Chemistry of Azoles and other Heterocycles with Two or more Heteroatoms.

36. Tandem Organic Reactions.

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Stuart Warren Cambridge University, UK.

Paul Wyatt School of Chemistry, University of Bristol, UK.
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