The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction

The novel synthesis of highly enantioenriched N-substituted α-amino-γ-alkyl(aryl)-γ-oxobutanoic acids is described. The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction. The role of retro-Mannich and retro-Michael reactions in th...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 21; no. 1; pp. 69 - 74
Main Authors Jakubec, Pavol, Petráš, Pavel, Ďuriš, Andrej, Berkeš, Dušan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2010
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
HOMOPHENYLALANINES
SIMULTANEOUS EPIMERIZATION
ALPHA-AMINO-ACIDS
ALDEHYDES
2 STEREOCENTERS
CONJUGATE ADDITION
AMIDES
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Summary:The novel synthesis of highly enantioenriched N-substituted α-amino-γ-alkyl(aryl)-γ-oxobutanoic acids is described. The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction. The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.12.014