The syntheses of a series of 1‐phenyl‐5‐phosphino 1,2,3‐triazoles are disclosed, within which, the phosphorus atom (at the 5‐position of a triazole) is appended by one, two or three triazole motifs, and the valency of the phosphorus(III) atom is completed by two, one or zero ancillary (phenyl or cyclohexyl) groups respectively. This series of phosphines was compared with tricyclohexylphosphine and triphenylphosphine to study the effect of increasing the number of triazoles appended to the central phosphorus atom from zero to three triazoles. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single‐crystal X‐ray diffraction structure determination. Gold(I) complexes were also prepared from 1‐(2,6‐dimethoxy)‐phenyl‐5‐dicyclohexyl‐phosphino 1,2,3‐triazole and 1‐(2,6‐dimethoxy)‐phenyl‐5‐diphenyl‐phosphino 1,2,3‐triazole ligands. The crystal structures thus obtained were examined using the SambVca (2.0) web tool and percentage buried volumes determined. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed. Furthermore, the regioselectivity of hydration of but‐1‐yne‐1,4‐diyldibenzene was probed.
Cyclopeptides (CPs) have been recognized as excellent templates for the rational design of biologically active compounds. However, in the absence of constraining elements, even the small cyclotetrapeptides (CTPs) and cyclopentapeptides (CPPs) may show conformational heterogeneity, with the occurrence of mixtures of cis/trans‐peptide bonds. In this paper, we discuss the synthesis of CTP and CPP model compounds containing 5‐aminomethyloxazolidine‐2,4‐dione (Amo)‐dipeptide scaffolds, which combine a β/α‐hybrid dipeptide structure & a Freidinger lactam‐like heterocycle. Depending on the stereochemistry, the dipeptide scaffolds were shown to efficiently promote well‐defined turn structures within the CP sequences, by taking advantage of the particular local constraints, and by establishing extra intramolecular hydrogen‐bonding interactions.
The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.
A series of phosphino triazoles are disclosed, within which, the phosphorus atom is appended by one, two or three triazole motifs. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single crystal X-ray diffraction structure determination. <i>SambVca</i> (2.0) was used to determine percentage buried volumes. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed.<br>
The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3-triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.
The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3-triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.
A series of phosphino triazoles are disclosed, within which, the phosphorus atom is appended by one, two or three triazole motifs. Gold(I) chloride complexes of the synthesised ligands were prepared and analysed by techniques including single crystal X-ray diffraction structure determination. <i>SambVca</i> (2.0) was used to determine percentage buried volumes. The effectiveness of these gold(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed.<br>
The synthesis of atropisomeric phoshino-triazoles is disclosed. It was found that intoduction of a phosphine functionality onto the 5-position of a 1,2,3-triazole ring the rotation around a triazole-aryl bond could...
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