Preface to the Fourth Edition
Part B emphasizes the most important reactions used in organic synthesis. The material is
organized by reaction type. Chapters 1 and 2 discuss the alkylation, conjugate addition and
carbonyl addition=condensation reactions of enolates and other carbon nucleophiles.
Chapter 3 covers the use of nucleophilic substitution, both at saturated carbon and at
carbonyl groups, in functional group of interconversions. Chapter 4 discusses electrophilic
additions to alkenes and alkynes, including hydroboration. Chapter 5 discusses reduction
reactions, emphasizing alkene and carbonyl-group reductions. Concerted reactions,
especially Diels±Alder and other cycloadditions and sigmatropic rearrangements, are
considered in Chapter 6. Chapters 7, 8, and 9 cover organometallic reagents and
intermediates in synthesis. The main-group elements lithium and magnesium as well as
zinc are covered in Chapter 7. Chapter 8 deals with the transition metals, especially copper,
palladium, and nickel. Chapter 9 discusses synthetic reactions involving boranes, silanes,
and stannanes. Synthetic reactions which involve highly reactive intermediatesÐcarboca-
tions, carbenes, and radicalsÐare discussed in Chapter 10. Aromatic substitution by both
electrophilic and nucleophilic reagents is the topic of Chapter 11. Chapter 12 discusses the
most important synthetic procedures for oxidizing organic compounds. In each of these
chapters, the most widely used reactions are illustrated by a number of speci®c examples
of typical procedures. Chapter 13 introduces the concept of synthetic planning, including
the use of protective groups and synthetic equivalents. Multistep syntheses are illustrated
with several syntheses of juvabione, longifolene, Prelog±Djerassi lactone, Taxol, and
epothilone. The chapter concludes with a discussion of solid-phase synthesis and its
application in the synthesis of polypeptides and oligonucleotides, as well as to combina-
torial synthesis.
The control of reactivity to achieve speci®c syntheses is one of the overarching goals
of organic chemistry. In the decade since the publication of the third edition, major
advances have been made in the development of ef®cient new methods, particularly
catalytic processes, and in means for control of reaction stereochemistry. For example, the
scope and ef®ciency of palladium- catalyzed cross coupling have been greatly improved by
optimization of catalysts by ligand modi®cation. Among the developments in stereocontrol
are catalysts for enantioselective reduction of ketones, improved methods for control of the
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