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6261006 
Book/Book Chapter 
2.16 The Bimolecular and Intramolecular Mannich and Related Reactions 
Akiyama, T 
2014 
Elsevier 
Amsterdam 
Comprehensive Organic Synthesis II (Second Edition) 
2 
629-681 
The Mannich reaction is a useful method for the preparation of β-amino carbonyl compounds of biological interest starting from aldehyde, amine, and carbonyl compounds. The classical Mannich reaction was limited to highly reactive aldehydes such as formaldehyde and acetaldehyde, a secondary amine. Development of the direct Mannich-type reaction expanded the scope of the Mannich reaction, and efficient method for the highly stereoselective Mannich-type reactions were extensively studied and reported. This chapter focuses on the enantioselective catalyzed version of the Mannich-type reactions, starting from the metal-catalyzed indirect and direct Mannich-type reactions. Vinylogous Mannich reactions are also included. Organocatalyzed Mannich-type reactions are compiled according to the catalysts employed: proline and derivatives, thiourea, cinchona alkaloid, Brønsted acid, and so on. 
Enamine; Mannich reaction; Metal catalyst; Organocatalyst; Vinylogous Mannich reaction 
Knochel, Paul