Volume 2 deals mainly with the addition reactions of delocalized carbanions (enolates) and their synthetic relatives (metalloenamines, enol ethers, allyl organometallics) with carbonyl compounds, imines and iminium ions. Major emphasis is placed on C-C bond-forming reactions such as the aldol and Mannich reactions. Acylation reactions are also included in this volume. Several topics that have not previously been reviewed are covered, including the use of enzymatic aldol reactions in synthesis and the Passerini-Ugi reactions.
Additions to C-X ?-Bonds, 1st Edition
Selected chapters: Uncatalyzed Additions of Nucleophilic Alkenes to C=X.
Allyl organometallics. Heteroatom-stabilized allylic anions. Propargyl and allenyl organometallics. The Aldol reaction: general acid and base catalysis. The Aldol reaction: group I and group II enolates. The Aldol reaction: group III enolates. Zinc enolates: the Reformatsky and Blaise Reactions. The Aldol reaction: transition metal enolates. The Knoevenagel reaction. The Perkin reaction. Darzens' glycidic ester condensation. Use of enzymatic Aldol reactions in synthesis. Metalloenamines. Hydrazone anions. Catalyzed Additions of Nucleophilic Alkenes to C=X.
The Prins and related reactions. Allylsilanes, allylstannanes and related systems. Asymmetric synthesis with enol ethers. Reactions of activated dienes with aldehydes. Addition-Elimination Reactions (Acylations).
The aliphatic Friedel-Crafts reaction. The biomolecular aromatic Friedel-Crafts reaction. The Reimer-Tiemann reaction. The Vilsmeier-Haack reaction. Acylation of esters, ketones and nitriles. The Eschenmoser coupling reaction. Additions of Nucleophilic Alkenes to C=NR and C=NR2+.
The bimolecular aliphatic Mannich and related reactions. The bimolecular aromatic Mannich reaction. The intramolecular Mannich and related reactions. Additions to N
-acyliminium ions. The Passerini and Ugi reactions. Author index. Subject index.