Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

Autor:	František Považanec, Peter Baran, Dušan Berkeš, Robert Manduch, Andrej Kolarovič
Rok vydání:	2005
Předmět:	Precipitation (chemistry) Chemistry Stereochemistry Aryl Organic Chemistry Hydrochloric acid Alkaline hydrolysis (body disposal) Catalysis law.invention Inorganic Chemistry chemistry.chemical_compound law Acid catalyzed Physical and Theoretical Chemistry Crystallization
Zdroj:	Tetrahedron: Asymmetry. 16:1927-1934
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2005.04.024
Popis:	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 cis-lactones, starting from both syn-2-amino-4-aryl-4-hydroxybutanoic acids and anti-2-amino-4-aryl-4-hydroxybutanoic acids or their mixtures. A highly diastereoselective two-step sequence (acid-catalyzed lactonization with CIAT process followed by alkaline hydrolysis) for the transformation of syn-3b–d to the corresponding anti-3b–d is reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a8e09e39988d35ab098684ef1970dfc7 https://doi.org/10.1016/j.tetasy.2005.04.024 Zobrazit plný text záznamu Full Text from ScienceDirect