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Six-Membered Transition States in Organic Synthesis

ISBN: 978-0-470-19904-6
200 pages
February 2008
Six-Membered Transition States in Organic Synthesis (0470199040) cover image


How stereoselective reactions occur through six-membered transition states

This book is a definitive guide for furthering 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

Includes "General Considerations" for each category in which the author presents computational studies that support a proposal of a six-membered state

Provides a thorough discussion of each reaction category, including an introduction and history, a discussion of the corresponding six-membered transition state, and details of synthetic applications in natural product synthesis

Incorporates real-life applications of these transition states to the total syntheses of biologically active natural products

Covers literature up to 2006, with the original references cited for further study

This is a premier reference for organic chemists, medicinal chemists, and physical organic chemists and researchers in industries and institutes focusing on fine chemicals, including pharmaceuticals, agriculture/biotech, and polymers/materials. It is also an illuminating text for upper-level undergraduate and graduate students in organic chemistry. The author's primary goal is to assist professors, researchers, and students in proposing reasonable transition states for the description of newly discovered stereo-selective reactions.
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Table of Contents



1 [3,3]-Sigmatropic Rearrangements.

General Considerations.


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.


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.


3.1 Boron Allylation Reaction.

3.2 Silicon Allylation Reaction.

4 Stereoselective Reductions.

General Considerations.


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.


Subject Index.

Scheme Index of Natural Products.

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Author Information

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.
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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)

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