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2.16 The Bimolecular and Intramolecular Mannich and Related Reactions

Authors
  • Akiyama, T.
Type
Book
Journal
Comprehensive Organic Synthesis
Publication Date
Jan 01, 2014
Pages
629–681
Identifiers
DOI: 10.1016/B978-0-08-097742-3.00220-2
ISBN: 978-0-08-097742-3
Source
Elsevier
Keywords
License
Unknown

Abstract

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.

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