Books by B. M. Trost

This volume contains 37 chapters on methods for reducing functional groups, organized into four main parts. (i) Reduction of C=X systems, where X is an electronegative heteroatom, divided into 14 chapters based on the degree of reduction, the oxidation level of the C=X substrate, and on the nature of the reagent. (ii) Reduction of X=Y systems, divided into three chapters, covering the reduction of such groups as nitro, azo, and the various kinds of P=O and S=O groups. (iii) Reduction of C=C and C≡C, divided into 12 chapters based on the method of reduction, with aromatic, heteroaromatic, and conjugated systems treated separately, and including an extensive discussion of hydrometallation. (iv) Reduction of single bonds, C-X to C-H, in eight chapters, including the hydrogenolysis of the various kinds of C-X bonds, the reduction of epoxides, and the reduction of vinyl derivatives to alkenes. Each chapter includes a discussion of chemoselectivity, regioselectivity, and stereoselectivity, wherever it is appropriate, and most include advice on the reagent of choice, and the mechanistic basis of the various methods of reduction. In short, it is, within the space available, as near to a comprehensive account of reduction in organic chemistry as one could hope for.

Volume 1 provides a detailed survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl functionality. Emphasis has been placed on those reagents that result in highly selective addition reactions. Methods are reported to select, for example, one carbonyl group over another in the same molecule, or to add preferentially a fragment to one (enantiotopic of diastereotopic) face of a carbonyl group. Processes that result from an initial addition to the C=X functional group, for example alkenations and rearrangements, are also covered in this volume.

This volume covers all methods of oxidation for use in organic synthesis. Emphasis has been placed on selectivity and functional group compatibility together with practical utility and applications. The volume is broadly divided to cover oxidation of unactivated carbon-hydrogen bonds, oxidation of activated carbon-hydrogen bonds, that is to say those adjacent to activating substituents and adjacent to heteroatoms, and oxidation of carbon-carbon double bonds. The volume also covers oxidation of C-X bonds, carbon-carbon single bonds, heteroatom oxidation and a number of special topics such as electrochemical methods, oxidative rearrangements, solid supported reagents, electron transfer oxidation, and biological methods.

Volume 3 covers carbon-to-carbon single bond forming reactions involving sp³, sp² and sp carbon centers, but only those which do not involve additions to C-X &pgr;-bonds. The volume first compares and contrasts the alkylation reactions of all types of sp³ carbon nucleophiles and also covers vinyl and alkynyl carbanions. Following on from Volume 2, a separate section covers Friedel-Crafts alkylation reactions, which is complemented by discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions leading to &agr;-bond formation, and involving all types of combinations ofsp³, sp² and sp carbon centers are next covered, including those reactions based on pinacol, acyloin and phenol oxidative coupling reactions, and also the Kolbe reaction. Rearrangement reactions, leading to carbon-to-carbon &agr;-bond formation, are often used in a clever manner in synthesis. The volume includes all those rearrangement reactions based on intermediate carbonium ions and carbanions, and also includes the benzil-benzilic acid and the Wolff rearrangements. The volume closes with coverage of carbonylation reactions, and the use of carbene insertion reactions into the C-H bond in synthesis.

In this volume, those functional groups containing heteroatoms that have gained importance in organic synthesis are dealt with in detail. The introduction of these various groups and their relevant transformations are described and the various aspects of chemoselectivity, regioselectivity and stereoselectivity are discussed. After a compilation of the synthetically most useful substitution processes, there is a series of chapters on the various types of acylation reactions and in this context the different methods of acyl group activation are discussed. As functional group protection is of very general importance for organic synthesis, a corresponding chapter is included. This is followed by a section on the preparation of carbonyl derivatives and the most important transformations and rearrangements of functional group derivatives. At the end of the volume one finds chapters on all types of elimination reactions and related thermal reactions together with a survey on fragmentation processes in organic synthesis.

Volume 4 focuses on additions and the resulting substitutions at carbon-carbon &pgr;-bonds. Part 1 includes processes generally considered as simple polar reactions, reactive electrophiles and nucleophiles adding to alkenes and alkynes. A major topic is Michael-type addition to electron deficient &pgr;-bonds, featured in the first six chapters. In part 2 are collected the four general processes leading to nucleophilic aromatic substitution, including radical chain processes and transition metal activation through to &pgr;-complexation. Metal-activated addition (generally by nucleophiles) to alkenes and polyenes is presented in part 3, including allylic alkylation catalyzed by palladium. The coverage of nonpolar additions in part 4 includes radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.

The guiding principle underlying the subject matter specifically compiled in Volume 5 has been to make available to the organic chemical community a sourcebook comprehensively covering all the important &pgr;-bond-dependent transformations. Thermal, photochemical, and metal-catalyzed cycloadditions of every major type are expertly detailed by the most knowledgeable researchers in these areas. The synthetically useful electrocyclic and sigmatropic processes where alkenic centers are intimately involved in the structural change are similarly canvassed in compact detail. With added attention given to ene reactions, small-ring rearrangements, and related transition metal-associated reactions, coverage has been achieved of the full range of organic transformations directly involving the rebonding of alkenic centers. As a consequence, this volume should serve as the comprehensive sourcebook of the field for the next decade and beyond.