3 article(s) from Hunter, Luke
Examples of conformationally biased amino acids [1-10]. Compound 6 is a target of this work.
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The first synthetic approach.
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The second synthetic approach.
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The third synthetic approach.
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The fourth synthetic approach (partially reproduced from ref. ).
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Selected J values and the inferred molecular conformations of 6a and 6b.
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Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228
Fluorination alters the reactivity of aziridines.
Fluorination makes β-lactam derivatives more reactive towards lipase-catalysed methanolysis.
The ring pucker in azetidine derivatives can be influenced by a C–F…N+ charge–dipole interaction.
Fluorination ridifies the pyrrolidine rings of ligand 10, with several consequences for its G-quadr...
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Proline 11 readily undergoes a ring-flip process, but (4R)-fluoroproline 12 is more rigid because o...
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Hyperconjugation rigidifies the ring pucker of a fluorinated organocatalyst 14, leading to higher e...
Fluorinated piperidines prefer the axial conformation, due to stabilising C–F…N+ interactions.
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Fluorination can rigidify a substituted azepane, but only if it acts in synergy with the other subs...
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The eight-membered N-heterocycle 24 prefers an axial orientation of the fluorine substituent, givin...
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Some iminosugars are “privileged structures” that serve as valuable drug leads.
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Fluorinated iminosugar analogues 32–34 illuminate the binding interactions of the α-glycosidase inh...
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Fluorinated miglitol analogues, and their inhibitory activity towards yeast α-glycosidase.
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Analogues of isofagomine (31) have different pKaH values, and therefore exhibit maximal β-glucosida...
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General strategy for the synthesis of fluorinated N-heterocycles via deoxyfluorination.
Late stage deoxyfluorination in the synthesis of multifunctional N-heterocycles.
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During the deoxyfluorination of N-heterocycles, neighbouring group participation can sometimes lead...
A building block approach for the synthesis of fluorinated aziridines 2 and 3.
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Building block approach for the synthesis of a difluorinated analogue of calystegine B (63).
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Synthesis of fluorinated analogues of brevianamide E (65) and gypsetin (68) via electrophilic fluor...
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Organocatalysed enantioselective fluorocyclisation.
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Synthesis of 3-fluoroazetidine 73 via radical fluorination.
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Synthesis of 3,3-difluoropyrrolidine 78 via a radical cyclisation.
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Chemoenzymatic synthesis of fluorinated β-lactam 4b.
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Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306
Conformational effects associated with C–F bonds.
HIV protease inhibitor Indinavir (17) and fluorinated analogues 18 and 19. In analogue 18 the gauche...
Cholesteryl ester transfer protein inhibitors 20 and 21. In the fluorinated analogue 21, nO→σ*CF hy...
HIV reverse transcriptase inhibitor 22 and acid-stable fluorinated analogues 23–25. The F–C–C–O gau...
Dihydroquinidine (26) and fluorinated analogues 27 and 28. Newman projections along the C9–C8 bonds...
The neurotransmitter GABA (29) and fluorinated analogues (R)-30 and (S)-30. Newman projections of (R...
The insect pheromone 31 and fluorinated analogues (S)-32 and (R)-32. The proposed bioactive conform...
Capsaicin (33) and fluorinated analogues (R)-34 and (S)-34.
Asymmetric epoxidation reaction catalysed by pyrrolidine 35. Inset: the geometry of the activated i...
The asymmetric transannular aldol reaction catalysed by trans-4-fluoroproline (41), and its applica...
The asymmetric Stetter reaction catalysed by chiral NHC catalysts 49–52. The ring conformations of ...
A multi-vicinal fluoroalkane.
X-ray crystal structures of diastereoisomeric multi-vicinal fluoroalkanes 55 and 56. The different ...
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Examples of fluorinated liquid crystal molecules. Arrows indicate the orientation of the molecular ...
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Di-, tri- and tetra-fluoro liquid crystal molecules 60–62.
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Collagen mimics of general formula (Pro-Yaa-Gly)10 where Yaa is either 4(R)-hydroxyproline (63) or ...
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Enkephalin-related peptide 64 and the fluorinated analogue 65. The electron-withdrawing trifluorome...
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The C–F bond influences the conformation of β-peptides. β-Heptapeptide 66 adopts a helical conforma...
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The conformations of pseudopeptides 69 and 70 are influenced by the α-fluoroamide effect and the fl...
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Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38
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