Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
| Autor: | Yoshizawa, Akina, Feula, Antonio, Male, Louise, Leach, Andrew G., Fossey, John S. |
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| Rok vydání: | 2018 |
| Předmět: |
Steric effects
Nitroaldol reaction Azetidine lcsh:Medicine 02 engineering and technology 010402 general chemistry 01 natural sciences Article Catalysis chemistry.chemical_compound Computational chemistry QD lcsh:Science Enantiomeric excess Multidisciplinary Nitromethane 010405 organic chemistry Chemistry lcsh:R Enantioselective synthesis 021001 nanoscience & nanotechnology Combinatorial chemistry 0104 chemical sciences lcsh:Q Flack parameter Enantiomer 0210 nano-technology |
| Zdroj: | Scientific Reports Yoshizawa, A, Feula, A, Male, L, Leach, A G & Fossey, J S 2018, ' Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform dfor asymmetric catalysis ', Scientific Reports, vol. 8 . https://doi.org/10.1038/s41598-018-24784-3 Scientific Reports, Vol 8, Iss 1, Pp 1-16 (2018) |
| ISSN: | 2045-2322 |
| Popis: | A series of single enantiomer, 2,4-cis-disubstituted amino azetidines were synthesised and used as ligands for copper-catalysed Henry reactions of aldehydes with nitromethane. Optimisation of ligand substituents and the reaction conditions was conducted. The enantiomeric excess of the formed products was highest when alkyl aldehydes were employed in the reaction (>99% e.e.). The absolute stereochemistry of one representative azetidine derivative salt was determined by analysis of the Flack parameter of an XRD single crystal structure. The origin of selectivity in catalysis was investigated computationally, revealing the importance of the amino-substituent in determining the stereochemical outcome. A racemic platinum complex of a cis-disubstituted azetidine is examined by XRD single crystal structure analysis with reference to its steric parameters, and analogies to the computationally determined copper complex catalyst are drawn. A preliminary example of the use of a cis-disubstituted azetidine scaffold in thiourea H-bonding catalyst is noted in the supporting information. |
| Databáze: | OpenAIRE |
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