Michael Addition
Jens Christoffers,
Jens Christoffers
Institut für Organische Chemie der Universität Stuttgart, Stuttgart, Germany
Search for more papers by this authorJens Christoffers,
Jens Christoffers
Institut für Organische Chemie der Universität Stuttgart, Stuttgart, Germany
Search for more papers by this authorFirst published: 15 July 2002
Abstract
The Michael reaction is defined as the conjugate 1,4-addition of carbon nucleophiles to acceptor-substituted CC bonds. Enolates of β-dicarbonyl compounds represent typical nucleophiles in this classical base-catalyzed CC-bond-forming reaction, yielding 1,5-dicarbonyl compounds as products. In some cases, metal catalysts as simple as FeCl3 ˙ 6 H2O can be applied, avoiding basic reaction conditions and thus resulting in an improved chemoselectivity compared with base catalysis. The Michael reaction can be performed in an intramolecular or vinylogous fashion, and is known as an elementary step in several reaction sequences. In most cases, Michael reaction products have at least one new stereogenic center. In order to achieve asymmetric reactions, chiral auxiliaries, chiral Brönstedt bases, or metal complexes bearing chiral ligands have been reported as catalysts for the Michael reaction.
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