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Search for "nitroalkenes" in Full Text gives 51 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

-generation catalyst for the Stetter reaction between aryl aldehydes (e.g. 47) and nitroalkenes (e.g. 48). Superficially, it seems that the bulky isopropyl group of 49 is solely responsible for the enantioselectivity of this reaction. However, the shape of the bicyclic ring system might also play a role and

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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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