Modern Aldol Reactions
Hardcover, 679 Pages, 2 Volumes
First Edition, June 2004
The complete spectrum of the aldol reaction is presented in this two-volume handbook. Top authors cover the fundamentals before moving on to enolates and catalytic reactions. Further sections are devoted to enzymatic as well as related reactions. A comprehensive overview of this important topic, removing the need for time-consuming research among the widely dispersed literature. With a foreword by Professor D. A. Evans.
The aldol addition has historically been the stepchild of organic synthesis. Even today, this reaction is run in teaching laboratories with standard procedures, and yields more or less of the condensation and polymerization side products, depending upon the skill of the student. Only with the advent of the natural product syntheses of the 20th century was this reaction studied closely and fundamentally improved. An important step was the prior formation of an enolate, which opened up new possibilities, e.g. the regioselective formation of enolates, and crossed aldol reactions with fewer restrictions on the choice of reactants. The stereoselectivity of the reaction can be explained with simple models, and methods became available in the meantime that would afford the formation of the desired syn- or anti-substituted aldol products.
Silyl enol ethers and the corresponding vinyl borates can also be used in place of the enolates; a major pioneer in this field, Teruaki Mukaiyama, was entrusted with the corresponding chapter in this book. A further refinement was the metal-catalyzed aldol addition, of special note in that it made possible enantioselective transformations. Here too, we read what the acknowledged experts have to say. These reactions have naturally found their way into the current literature, and are already well known to some readers, but this monograph offers copious supplementary information. It is amazing that Rainer Mahrwald has been able to organize such a comprehensive overview, which even encompasses biocatalyzed reactions.
The book "Modern Aldol Reactions" is truly one of a kind, a most successful compilation of the various methods for preparing aldols. The aldol addition is of immense importance in the synthesis of natural products and bioactive substances, and this up-to-date work comprises a vast body of knowledge that is of unquestionable value to chemists in the two areas just mentioned. Furthermore, the introductory chapter and the excellent reviews provide all the information necessary to be able to select two or three interesting reactions for any synthesis problem. An additional strength is that each chapter contains from 3-5 sample experimental procedures.
Fundamentals and Transition State Models
The Development of Titanium Enolate Based Aldol Reactions
Boron and Silicon Enolates in Crossed Aldol Reaction
Silver, Gold and Palladium Lewis-Acids
Boron and Silicon Lewis Acids for Mukaiyama Aldol Reactions
Copper Lewis Acids
Tin-promoted Aldol Reactions and Their Applications to Total Syntheses of Natural Products
Zirconium Alkoxides as Lewis Acids
Direct Catalytic Asymmetric Aldol Reaction Using Chiral Metal Complexes
Catalytic Enantioselective Aldol Additions with Chiral Lewis Bases
Amine-Catalyzed Aldol Reactions
Enzyme Catalyzed Aldol Additions
Antibody-Catalyzed Aldol Reactions
The Aldol-Tishchenko Reaction
The Aldol Reaction in Natural Product Synthesis: The Epothilone Story