Comprehensive Organic Synthesis: Reduction

Trost B.M., Fleming I. (eds.)0080405991

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.