Organic Synthesis: Strategy and Control

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Product Description

Organic Synthesis: Strategy and Control is the long-awaited sequel to Stuart Warren� �s bestseller Organic Synthesis: The Disconnection Approach, which looked at the planning behind the synthesis of compounds. This unique book now provides a comprehensive, practical account of the key concepts involved in synthesising compounds and 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.

• A comprehensive, practical account of the key concepts involved in synthesising compounds
• Takes a mechanistic approach, which explains reactions and gives guidelines on how reactions might behave in different situations
• Focuses on reactions that really work rather than those with limited application
• Contains extensive, up-to-date references in each chapter

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.

Organic Synthesis: Strategy and Control Review

I am a graduate student and have invested in a number of textbooks dealing with this topic. While there are a number of more comprehensive books for literature references, such as March's book or Smith's 'Organic Synthesis,' Warren's books should have great appeal to student's trying to learn this subject. I originally came across his 1984 book "The Disconnection Approach" and was impressed by how engaging it was and how clearly the logic progressed from one chapter to the next. That book was recently rereleased as an updated edition, where Paul Wyatt appeared as coauthor, in January of 2009. It serves as an excellent bridge between undergraduate education and problems faced by real practitioners, as it identifies many problems of selectivity that are either overlooked - or simply too advanced to address - at the (American) undergraduate level. "The Disconnection Approach" identifies many of the fundamental problems faced by practitioners, but by and large does not stray from the complement of reactions learned at the undergraduate level, which is why I describe it as a "bridge" book. It leaves out many of the modern methods practitioners would use to solve synthetic problems. "Strategy and Control" addresses those modern methods in the context of the specific problems that they resolve.

Warren and Wyatt's book may only have 40-50 references a chapter, compared to the hundreds for March's and Smith's, but this is a calculated move on their part, and what is lost in breadth is easily regained in clarity. This serves to fill a rather overlooked niche in textbooks for upper level courses - teaching! What you will not find in this book are lists of 30-40 different ways to do a Pauson-Khand reaction, a Witting reaction, a Claisen rearrangement, etc. and the optimized conditions for each example without regard to what the reaction has achieved in the particular synthesis in which it was used. "Strategy and Control" uses synthetic strategy and reaction control, rather than reaction type, as it's organizing principles. Warren and Wyatt focus on the logic of synthesis, rather than trying to introduce students to every possible reaction available, recognizing that other books and review articles have been written for this purpose. They have a commitment to showing the student each step in a reaction series, and the book is full of beautifully crafted schemes and tables. The integration of arrow pushing for the reaction mechanisms and detailed retrosynthetic/synthetic pathways never leaves you wondering "How did that happen?" The additional workbook is definitely one of the better ones available, providing detailed answers to problems often without the need of a trip to the library and the good judgment to suggest when that trip might be beneficial or necessary.

The book is broken up into five major sections:
1) Selectivity
2) Making Carbon-Carbon Bonds
3) Carbon-Carbon Double Bonds
4) Stereochemistry
5) Functional Group Strategy

The first section on selectivity introduces the concepts of chemoselectivity, regioselectivity and stereoselectivity in the context of synthetic problems. Wyatt and Warren's knowledge of the chemical literature shines through here, as they pick both classic (Corey's longifolene) and current (Pfizer's Viagra) syntheses as illustrations. Under this section, synthetic strategy and planning are also discussed. One of the more memorable discussions appears in chapter 5, where a substituted enone is fully disconnected and the various strategies for making each of the retro synthetic disconnections work in the forward manner is briefly discussed. This discussion sets the stage for several of the topics in the next two major sections which describe making single and double carbon-carbon bonds.

In the second section, the focus is largely on the reaction of carbonyl compounds or their synthetic equivalents, with chapters discussing the control of the Michael reaction, specific enol equivalents, extended enolates, homoenolates, and acyl anion equivalents. Additionally, there is a chapter about allyl anions, a chapter about metal sigma-complexes, and a chapter about selectively producing ortho-substituted aromatic compounds.

The third section begins with a discussion of the synthesis of double bonds with defined stereochemistry. It then has separate chapters that investigate vinyl anion equivalents, electrophilic attack on alkenes, Pd C-C coupling chemistry in the context of vinyl cation precursors, and the synthetic uses of allyl alcohols.

The fourth section about stereochemistry is an excellent introduction to the ways in which modern sythesis is affected by stereochemical problems. It begins with a discussion that focuses on the vocabulary of stereochemistry and also addresses several general stereochemical principles and common misconceptions. The bulk of the section then focuses on three general topics - resolution, the chiral pool, and asymmetric induction. Under resolution, the authors address classic, kinetic and dynamic kinetic resolutions of stereochemical mixtures. The chapters about the chiral pool focus on the (readily) available members of this class of compounds and their uses in synthesis. Both reagent-based and substrate-based asymmetric induction are discussed in several chapters and the section ends with discussion of synthetic strategy in the context of assymetric synthesis.

The final section on functional group strategy focuses on improving known reactions, or forcing a reaction, through mechanistic thinking. The section focuses quite a bit on heterocyclic functionalisation chemistry with some discussion on oxidation of aromatics, enols and enolates (oxygen electrophiles RO+). Pericyclic chemistry with heteroatoms also appears as a topic here. The book ends with a discussion of tandem reaction strategies.

The book assumes readers have already been introduced to the retrosynthetic tools described in "The Disconnection Approach" and so it is recommended by the authors that students become familiar with those concepts before progressing on to this text. While the need to obtain two books for a course may seem excessive, it is a worthwhile investment in my opinion, as Warren and Wyatt are excellent teachers and these books could not do a better job in selecting examples from the literature. Both books are very readable and provide the most painless introduction to this often overwhelming subject.

The hard cover copy is beautiful book with a solid binding. It should serve as an excellent accompaniment to any graduate synthesis course.

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