Six-Membered Transition States in Organic Synthesis

Jaemoon Yang, PhD, is a lecturer in organic chemistry at Montana State University in Bozeman, Montana. Dr. Yang was born in South Korea; he earned his PhD under Dr. Craig Wilcox at the University of Pittsburgh in 2000. Following a postdoctoral fellowship with Dr. Huw Davies at SUNY Buffalo, Dr. Yang started teaching organic chemistry and conducting research on asymmetric hydroamination via chiral lanthanide complexes at Montana State University with Dr. Tom Livinghouse.

• 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.

Fifty years ago, Zimmerman and Traxler put forth an audacious suggestion that in a reaction they were studying six of the atoms were oriented in a ring as the two components approached each other. This was at a time when no one considered the detailed orientation of molecules during reactions. This Zimmerman-Traxler hypothesis is now known to be not only correct for their reaction, but in fact true in many other chemical processes. As such, the idea is one of the fundamental organizing principles of organic chemistry. Yang (Montana State Univ.) has provided a useful collection of all reactions currently understood to proceed in such fashion. These reactions are contained in 4 chapters: "[3,3] - Sigmatrophic Rearrangements," "Aldol Reactions," "Metal Allylation Reactions," and "Stereoselective Reductions." This small book should be useful for both synthetic chemists and those studying mechanisms, particularly stereochemistry, of organic reactions. Summing Up: Recommended. Upper-division undergraduate through professional collections. -- A. Fry, Wesleyan University (CHOICE, March 2009) It is an interesting, well-written, and carefully researched book, full of useful details for practioners and students of organic chemistry. (Journal of the American Chemical Association, July 2, 2008)