The Experts below are selected from a list of 726 Experts worldwide ranked by ideXlab platform
John Fossey - One of the best experts on this subject based on the ideXlab platform.
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Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.
Frontiers in chemistry, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N’-palladium(II) chloride complexes, one N,N’-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Two platinum(II) chloride N,N’-complexes of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN’ metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalised metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
Scientific Reports, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_1_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.PDF
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_3_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.ZIP
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
Akina Yoshizawa - One of the best experts on this subject based on the ideXlab platform.
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Azetidines for asymmetric synthesis
2018Co-Authors: Akina YoshizawaAbstract:The creation of asymmetric ligands with lower environmental impact is important, as such chiral N,N’ ligands attract some attention. A new method for the synthesis of 1,2,4-trisubstituted amino Azetidines with \(cis\) relative configuration across its two stereogenic centres was reported in 2013. Due to this \(cis\) conformation, the azetidine compounds are expected to be good chiral ligands for asymmetric catalysis. The nitro aldol (Henry) reaction is an established method for producing new carbon-carbon bonds and is a key reaction in the synthesis of many important compounds. Enantioselective Henry reactions generate carbon-carbon bonds and our Azetidines are probed as ligands for that reaction. In this work, new Azetidines and their palladium and platinum complexes were prepared and characterised by techniques including X-ray diffraction, confirming retention of the \(cis\) conformation. Furthermore, enantiopure \(cis\)-Azetidines were used as chiral ligands for a range of transition metals including the use of Cu-azetidine complexes as catalysts for the Henry reaction, in up to >99.5% ee. New enantiopure amino Azetidines and their transition metal complexes are demonstrated as asymmetric catalysts for the asymmetric Henry reaction.
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Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.
Frontiers in chemistry, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N’-palladium(II) chloride complexes, one N,N’-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Two platinum(II) chloride N,N’-complexes of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN’ metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalised metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
Scientific Reports, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_1_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.PDF
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
Antonio Feula - One of the best experts on this subject based on the ideXlab platform.
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Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.
Frontiers in chemistry, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N’-palladium(II) chloride complexes, one N,N’-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Two platinum(II) chloride N,N’-complexes of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN’ metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalised metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
Scientific Reports, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_1_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.PDF
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_3_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.ZIP
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
James A Bull - One of the best experts on this subject based on the ideXlab platform.
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short synthesis of oxetane and azetidine 3 aryl 3 carboxylic acid derivatives by selective furan oxidative cleavage
Organic Letters, 2020Co-Authors: Maryne A J Dubois, Milo A Smith, Andrew J P White, Alvin Lee Wei Jie, James J Mousseau, Chulho Choi, James A BullAbstract:Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, Azetidines, and cyclobutanes are p...
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Synthesis of 3-Aryl-3-Sulfanyl Azetidines by Iron-Catalyzed Thiol Alkylation with N-Cbz Azetidinols.
The Journal of organic chemistry, 2019Co-Authors: Maryne A J Dubois, James J Mousseau, Chulho Choi, Anna Lazaridou, James A BullAbstract:New small-ring derivatives can provide valuable motifs in new chemical space for drug design. 3-Aryl-3-sulfanyl Azetidines are synthesized directly from azetidine-3-ols in excellent yield by a mild Fe-catalyzed thiol alkylation. A broad range of thiols and azetidinols bearing electron-donating aromatics are successful, proceeding via an azetidine carbocation. The N-carboxybenzyl group is a requirement for good reactivity and enables the NH-azetidine to be revealed. Further reactions of the azetidine sulfides demonstrate their potential for incorporation in drug discovery programs.
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Synthesis of 3‑Aryl-3-Sulfanyl Azetidines by Iron-Catalyzed Thiol Alkylation with N‑Cbz Azetidinols
2019Co-Authors: Maryne A. J. Dubois, Chulho Choi, James J Mousseau, Anna Lazaridou, James A BullAbstract:New small-ring derivatives can provide valuable motifs in new chemical space for drug design. 3-Aryl-3-sulfanyl Azetidines are synthesized directly from azetidine-3-ols in excellent yield by a mild Fe-catalyzed thiol alkylation. A broad range of thiols and azetidinols bearing electron-donating aromatics are successful, proceeding via an azetidine carbocation. The N-carboxybenzyl group is a requirement for good reactivity and enables the NH-azetidine to be revealed. Further reactions of the azetidine sulfides demonstrate their potential for incorporation in drug discovery programs
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Synthesis of 3,3-DiarylAzetidines by Calcium(II)-Catalyzed Friedel–Crafts Reaction of Azetidinols with Unexpected Cbz Enhanced Reactivity
2018Co-Authors: Camille Denis, Maryne A J Dubois, James J Mousseau, Chulho Choi, Anne-sophie Voisin-chiret, Ronan Bureau, James A BullAbstract:Azetidines are valuable motifs that readily access under explored chemical space for drug discovery. 3,3-DiarylAzetidines are prepared in high yield from N-Cbz azetidinols in a calcium(II)-catalyzed Friedel–Crafts alkylation of (hetero)aromatics and phenols, including complex phenols such as β-estradiol. Electron poor phenols undergo O-alkylation. The product Azetidines can be derivatized to drug-like compounds through the azetidine nitrogen and the aromatic groups. The N-Cbz group is crucial to reactivity by providing stabilization of an intermediate carbocation on the four-membered ring
Louise Male - One of the best experts on this subject based on the ideXlab platform.
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Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.
Frontiers in chemistry, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N’-palladium(II) chloride complexes, one N,N’-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Two platinum(II) chloride N,N’-complexes of 2,4-cis-Azetidines where prepared and analysed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN’ metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalised metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
Scientific Reports, 2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_1_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.PDF
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.
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Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract: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.
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Data_Sheet_3_Palladium and Platinum 2,4-cis-amino Azetidine and Related Complexes.ZIP
2018Co-Authors: Akina Yoshizawa, Antonio Feula, Louise Male, Andrew G. Leach, John FosseyAbstract:Seven N,N'-palladium(II) chloride complexes, one N,N'-palladium(II) acetate complex of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Two platinum(II) chloride N,N'-complexes of 2,4-cis-Azetidines where prepared and analyzed by single crystal XRD. Computational analysis and determination of the %Vbur was examined conducted. A CNN' metallocyclic complex was prepared by oxidative addition of palladium(0) to an ortho bromo 2,4-cis-disubstituted azetidine and its crystal structure displays a slightly pyramidalized metal-ligand orientation.