Asymmetric Malonic and Acetoacetic Acid Syntheses - A Century of Enantioselective Decarboxylative Protonations

The enantioselective decarboxylative protonation (EDP) of malonic or acetoacetic acid derivatives is a synthetic methodology by which the chirality of the product is generated during the enol/enolate protonation step. Although EDP is a century‐old reaction, it has not received much attention until r...

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Veröffentlicht in:European Journal of Organic Chemistry 2008-11, Vol.2008 (33), p.5493-5506
Hauptverfasser: Blanchet, Jérôme, Baudoux, Jérôme, Amere, Mukkanti, Lasne, Marie-Claire, Rouden, Jacques
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Sprache:eng
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Zusammenfassung:The enantioselective decarboxylative protonation (EDP) of malonic or acetoacetic acid derivatives is a synthetic methodology by which the chirality of the product is generated during the enol/enolate protonation step. Although EDP is a century‐old reaction, it has not received much attention until recently. This review focuses on the EDP as an alternative to the strong‐base‐mediated deprotonation/asymmetric reprotonation for the stereocontrol of C–H bond formation. The diverse synthetic approaches are classified according to the type of catalysis used, which are organic, metallic or enzymatic.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) The enantioselective decarboxylative protonation (EDP) of malonic or acetoacetic acid derivatives is a synthetic methodology by which the chirality of the product is generated during the enolate protonation step. This review focuses on the enantioselective decarboxylative protonation for the stereocontrol of C–H bond formation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800759