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Mannich Reaction

(Mannich Condensation, Mannich Aminomethylation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr409

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Mannich Reaction. Comprehensive Organic Name Reactions and Reagents. 409:1820–1828.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is a multicomponent condensation between an amine, an enolizable carbonyl compound (donor), and a nonenolizable carbonyl compound (acceptor) to form a β-amino carbonyl compound (ketone or ester), with the concomitant formation of both carbon-carbon and carbon-nitrogen bonds and is known as the Mannich reaction, or Mannich condensation. Several variants of this reaction have been discussed. The Mannich reaction occurs under very simple conditions and gives desired compounds in high yields with two potential chiral centers. This reaction has been extensively modified beside the variant reactions. Several conditions of this reaction have been discussed to enhance stereoselectivity as well as the final yield. This reaction has been used for the preparation of stereoselective compounds under catalytic conditions.

Keywords:

  • 2,6-dinitrophenol;
  • 6-amino-α,β-unsaturated carbonyl compound;
  • methoxytris-(pentafluorophenyl)silane;
  • lewis acids