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Asymmetric Malonic and Acetoacetic Acid Syntheses – A Century of Enantioselective Decarboxylative Protonations
Author(s) -
Blanchet Jérôme,
Baudoux Jérôme,
Amere Mukkanti,
Lasne MarieClaire,
Rouden Jacques
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800759
Subject(s) - enantioselective synthesis , chemistry , protonation , malonic acid , deprotonation , enol , acetoacetic ester synthesis , decarboxylation , chirality (physics) , organic chemistry , catalysis , stereochemistry , chiral symmetry , ion , physics , quantum mechanics , nambu–jona lasinio model , quark
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)
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