861896-81-3Relevant academic research and scientific papers
The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction
Jakubec, Pavol,Petras, Pavel,Duris, Andrej,Berkes, Dusan
experimental part, p. 69 - 74 (2010/04/24)
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.
Crystallization-induced asymmetric transformations (CIAT): Stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids
Berkes, Dusan,Kolarovic, Andrej,Manduch, Robert,Baran, Peter,Povazanec, Frantisek
, p. 1927 - 1934 (2007/10/03)
Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble
