Six-Membered Transition States in Organic Synthesis

This book furthers readers’ understanding of the amazing features of six-membered transition states in stereoselective organic reactions. Comprehensive and logically organized, it covers reactions classified in four categories: [3,3]-sigmatropic rearrangements, aldol reactions, metal allylation reactions, and stereoselective reductions. There is a thorough discussion of each reaction category, along with computational studies that support a proposal of a six-membered state. The book assists professors, researchers, and students in proposing reasonable transition states for the description of newly discovered stereoselective reactions.

Preface. Introduction. 1 [3,3]-Sigmatropic Rearrangements. General Considerations. Reactions. 1.1 Claisen Rearrangement. 1.2 Johnson–Claisen Rearrangement. 1.3 Ireland–Claisen Rearrangement. 1.4 Cope Rearrangement. 1.5 Anionic Oxy-Cope Rearrangement. 1.6 Aza-Cope–Mannich Reaction. 2 Aldol Reactions. General Considerations. Reactions. 2.1 Asymmetric Syn-Aldol Reaction. 2.2 Asymmetric Anti-Aldol Reaction. 2.3 Proline-Catalyzed Asymmetric Aldol Reaction. 3 Metal Allylation Reactions. General Considerations. Reactions. 3.1 Boron Allylation Reaction. 3.2 Silicon Allylation Reaction. 4 Stereoselective Reductions. General Considerations. Reactions. 4.1 Diastereoselective Syn-Reduction of β-Hydroxy Ketones. 4.2 Diastereoselective Anti-Reduction of β-Hydroxy Ketones. 4.3 Asymmetric Reduction. List of Copyrighted Materials. Abbreviations. Subject Index. Scheme Index of Natural Products.