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Search for "advanced materials" in Full Text gives 76 result(s) in Beilstein Journal of Organic Chemistry.

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The C–F bond as a conformational tool in organic and biological chemistry

Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

Luke Hunter School of Chemistry, The University of Sydney, NSW 2006, Australia 10.3762/bjoc.6.38 Abstract Organofluorine compounds are widely used in many different applications, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers. It has been recognised for many

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Graphical Abstract

Figure 1: Conformational effects associated with C–F bonds.

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Figure 2: HIV protease inhibitor Indinavir (17) and fluorinated analogues 18 and 19. In analogue 18 the gauche...

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Figure 3: Cholesteryl ester transfer protein inhibitors 20 and 21. In the fluorinated analogue 21, n_O→σ*_CF hy...

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Figure 4: HIV reverse transcriptase inhibitor 22 and acid-stable fluorinated analogues 23–25. The F–C–C–O gau...

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Figure 5: Dihydroquinidine (26) and fluorinated analogues 27 and 28. Newman projections along the C9–C8 bonds...

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Figure 6: The neurotransmitter GABA (29) and fluorinated analogues (R)-30 and (S)-30. Newman projections of (R...

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Figure 7: The insect pheromone 31 and fluorinated analogues (S)-32 and (R)-32. The proposed bioactive conform...

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Figure 8: Capsaicin (33) and fluorinated analogues (R)-34 and (S)-34.

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Figure 9: Asymmetric epoxidation reaction catalysed by pyrrolidine 35. Inset: the geometry of the activated i...

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Figure 10: The asymmetric transannular aldol reaction catalysed by trans-4-fluoroproline (41), and its applica...

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Figure 11: The asymmetric Stetter reaction catalysed by chiral NHC catalysts 49–52. The ring conformations of ...

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Figure 12: A multi-vicinal fluoroalkane.

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Figure 13: X-ray crystal structures of diastereoisomeric multi-vicinal fluoroalkanes 55 and 56. The different ...

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Figure 14: Examples of fluorinated liquid crystal molecules. Arrows indicate the orientation of the molecular ...

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Figure 15: Di-, tri- and tetra-fluoro liquid crystal molecules 60–62.

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Figure 16: Collagen mimics of general formula (Pro-Yaa-Gly)₁₀ where Yaa is either 4(R)-hydroxyproline (63) or ...

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Figure 17: Enkephalin-related peptide 64 and the fluorinated analogue 65. The electron-withdrawing trifluorome...

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Figure 18: The C–F bond influences the conformation of β-peptides. β-Heptapeptide 66 adopts a helical conforma...

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Figure 19: The conformations of pseudopeptides 69 and 70 are influenced by the α-fluoroamide effect and the fl...

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Review

Published 20 Apr 2010

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