Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis

Research output: Contribution to journalArticle

Standard

Rigid and concave, 2,4-cis-substituted azetidine derivatives : A platform for asymmetric catalysis. / Yoshizawa, Akina; Feula, Antonio; Male, Louise; Leach, Andrew G; Fossey, John S.

In: Scientific Reports, Vol. 8, No. 1, 6541, 25.04.2018.

Research output: Contribution to journalArticle

Harvard

APA

Vancouver

Author

Yoshizawa, Akina ; Feula, Antonio ; Male, Louise ; Leach, Andrew G ; Fossey, John S. / Rigid and concave, 2,4-cis-substituted azetidine derivatives : A platform for asymmetric catalysis. In: Scientific Reports. 2018 ; Vol. 8, No. 1.

Bibtex

@article{6a51a61e57c247c5b676ecc3b70d3228,
title = "Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis",
abstract = "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.",
author = "Akina Yoshizawa and Antonio Feula and Louise Male and Leach, {Andrew G} and Fossey, {John S}",
year = "2018",
month = apr,
day = "25",
doi = "10.1038/s41598-018-24784-3",
language = "English",
volume = "8",
journal = "Scientific Reports",
issn = "2045-2322",
publisher = "Nature Publishing Group",
number = "1",

}

RIS

TY - JOUR

T1 - Rigid and concave, 2,4-cis-substituted azetidine derivatives

T2 - A platform for asymmetric catalysis

AU - Yoshizawa, Akina

AU - Feula, Antonio

AU - Male, Louise

AU - Leach, Andrew G

AU - Fossey, John S

PY - 2018/4/25

Y1 - 2018/4/25

N2 - 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.

AB - 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.

U2 - 10.1038/s41598-018-24784-3

DO - 10.1038/s41598-018-24784-3

M3 - Article

C2 - 29695806

VL - 8

JO - Scientific Reports

JF - Scientific Reports

SN - 2045-2322

IS - 1

M1 - 6541

ER -