We are pleased to provide the following series of chemistry handouts to anyone who might benefit from reading them and do so free of charge. The handouts have been extensively updated to introduce new topics and provide the latest, best summaries of the chemistry literature. These handouts were created as part of an advanced course on the synthesis of complex molecules. Many individuals participated in creating these handouts and wherever possible we have attempted to identify co-authors at the bottom of the relevant documents. We would like to acknowledge with gratitude the efforts of a number of Pfizer scientists who selflessly gave of their free time to help with the latest updates; they are acknowledged within the handouts. Over several years we have received many requests to permit these handouts to be used in ongoing courses in many different institutions. These requests have always been granted. Please feel free to use these materials to further chemistry teaching. We welcome corrections, comments, and ideas to improve the handouts.
1. Lithium-Halogen Exchange
2. Organolithium Reagents
3. Directed Ortho Metalation
4. Magnesium-Halogen Exchange
5. Reduction
6. Oxidation
7. Protective Groups – Silicon-Based Protection of the Hydroxyl Group
8. Birch Reduction
9. Asymmetric Alkylation of Enolates
10. Stereoselective, Directed Aldol Reaction
11. The Stille Reaction
12. The Suzuki Reaction
13. The Heck Reaction
14. Asymmetric Allylation Reactions
15. Synthesis of Chiral Amines by Asymmetric Additions to tert-Butylsulfinimines (Ellman Auxiliary)
16. The Nozaki–Hiyama–Kishi Reaction, Asymmetric Additions to Carbonyl Compounds
17. Organozinc Reagents: Asymmetric Additions to Carbonyl Compounds
18. The Noyori Asymmetric Hydrogenation Reaction
19. Stereoselective Olefination Reactions: The Wittig Reaction
20. Hydrozirconation and Carbozirconation
21. C–N Bond-Forming Reactions: Reductive Amination
22. C–O Bond-Forming Reactions: SN2 Reactions
23. Sharpless Asymmetric Epoxidation Reaction
24. Sharpless Asymmetric Dihydroxylation Reaction
25. Shi Asymmetric Epoxidation Reaction
26. Transformations of 2,3-Epoxy Alcohols
27. Asymmetric Diels–Alder Reactions
28. Anionic Cyclization Reactions
29. Cyclopropanation
30. Cyclobutane Synthesis
31. 5-Membered Ring Synthesis by Radical Cyclization
32. The Olefin Metathesis Reaction
33. Methods for Ring Contraction