Diastereoselective synthesis of β-lactams via Kinugasa reaction of acyclic chiral nitrones
| Autor: | Jadwiga Frelek, Łukasz Mucha, Olga Staszewska-Krajewska, Sebastian Stecko, Kamil Parda, Marek Chmielewski, Bartłomiej Furman, Artur Ulikowski, Agata Suszczyńska |
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| Rok vydání: | 2016 |
| Předmět: |
Circular dichroism
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Absolute configuration chemistry.chemical_element Nuclear magnetic resonance spectroscopy 010402 general chemistry 01 natural sciences Copper Combinatorial chemistry Catalysis 0104 chemical sciences Inorganic Chemistry β lactams Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry. 27:12-21 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2015.11.006 |
| Popis: | An approach to β-lactams via a Kinugasa reaction between chiral copper acetylides and chiral acyclic nitrones bearing either 1,3-dioxane or 1,3-dioxolane moieties is reported. The stereochemical preferences observed in these reactions are discussed. The reaction provides access to a variety of interesting β-lactam structures. Electronic circular dichroism in combination with NMR spectroscopy was shown to be a useful and effective method for the reliable determination of the absolute configuration of all components of a complex mixtures of azetidinones. The effectiveness of the chiral analysis of complex mixtures was demonstrated for HPLC coupled on-line with electronic circular dichroism detection as well. |
| Databáze: | OpenAIRE |
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