Organic stereochemistry. Part 3: Other stereogenic elements: Axes of chirality, planes of chirality, helicity, and (E,Z)-diastereoisomerism

Helvetica Chimica Acta

Volumn 96, Issue 3, 2013, Pages 351-374

  Testa, Bernard ^a  

^a LAUSANNE UNIVERSITY HOSPITAL   (Switzerland)

Author keywords

Stereoisomerism; Symmetry elements; tereochemistry

Indexed keywords

BIO-SYSTEMS; DIASTEREOISOMERISM; DOUBLE BONDS; ISOMERIZATION REACTION; ORGANIC STEREOCHEMISTRY; STEREOGENIC CENTERS; STEREOISOMERISM; TEREOCHEMISTRY;

ISOMERIZATION; STEREOCHEMISTRY; STEREOSELECTIVITY;

CHIRALITY;

1 (2,6 DIFLUOROBENZYL) 3 [2 AMINO 2 PHENYLETHYL] 5 (2 FLUORO 3 METHOXYPHENYL) 6 METHYLURACIL; ALKYLIDENE DERIVATIVE; ALLENE DERIVATIVE; BENZOANTHRACENE DERIVATIVE; CEPHALOCHROMIN; CYCLOOCTENE; DNA; ELEMENT; GLUTINIC ACID; GOSSYPOL; HEXAHELICENE; HYPERICIN; NATURAL PRODUCT; SPIRANE DERIVATIVE; STEREOGENIC ELEMENT; UNCLASSIFIED DRUG;

CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REVIEW; STEREOISOMERISM; SUBSTITUTION REACTION;

EID: 84875238722     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200471     Document Type: Review

References (66)

1. G. Krow, 'The Determination of Absolute Configuration of Planar and Axially Dissymmetric Molecules', Topics Stereochem. 1970, 5, 31-68.
2. D. G. Morris, 'Stereochemistry', The Royal Society of Chemistry, London, 2001, 170 p.
3. E. L. Eliel, S. H. Wilen, M. P. Doyle, 'Basic Organic Stereochemistry', John Wiley & Sons, 2001, 704 p.
4. E. L. Eliel, S. H. Wilen, 'Stereochemistry of Organic Compounds', John Wiley & Sons, 1994, 1267 p.
5. B. Testa, 'The Geometry of Molecules: Basic Principles and Nomenclatures', in 'Stereochemistry', Ed. C. Tamm, Elsevier, Amsterdam, 1982, pp. 1-47.
6. B. Testa, 'Principles of Organic Stereochemistry', Dekker, New York, 1979, 248 p.
7. F. D. Gunstone, 'Guidebook to Stereochemistry', Longman, London, 1975, 110 p.
8. K. Mislow, 'Introduction to Stereochemistry', Benjamin, New York, 1966, 193 p.
9. International Union of Pure and Applied Chemistry (IUPAC), Organic Chemistry Division, 'Basic Terminology of Stereochemistry', http://www.chem. qmul.ac.uk/iupac/stereo/, last accessed January 2013.
10. International Union of Pure and Applied Chemistry (IUPAC), 'Recommendations 1996-Basic Terminology of Stereochemistry', Pure Appl. Chem. 1996, 68, 2193-2222.
11. International Union of Pure and Applied Chemistry (IUPAC), Organic Chemistry Division, 'Rules for the Nomenclature of Organic Chemistry-Section E: Stereochemistry', Pure Appl. Chem. 1976, 45, 13-30.
12. International Union of Pure and Applied Chemistry (IUPAC), 'Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993)', Blackwell Scientific Publications, Oxford, 1993.
13. International Union of Pure and Applied Chemistry (IUPAC), 'Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H', Pergamon Press, Oxford, 1979.
14. A. D. McNaught, A. Wilkinson, 'Compendium of Chemical Terminology', 2nd edn. (the IUPAC 'Gold Book'), Blackwell Scientific Publications, Oxford, 1997; XML on-line corrected version, http://goldbook.iupac.org; (last accessed December 2012) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins, doi: 10.1351/goldbook.
15. R. S. Cahn, 'An Introduction to the Sequence Rule-A System for the Specification of Absolute Configuration', J. Chem. Educ. 1964, 41, 116-125.
16. R. S. Cahn, C. Ingold, V. Prelog, 'Specification of Molecular Chirality', Angew. Chem., Int. Ed. 1966, 5, 385-415, 511.
17. V. Prelog, G. Helmchen, 'Basic Principles of the CIP-System and Proposals for a Revision', Angew. Chem., Int. Ed. 1982, 21, 567-583.
18. H. Hirschmann, K. R. Hanson, 'Elements of Stereoisomerism and Prostereoisomerism', J. Org. Chem. 1971, 36, 3293-3306.
19. H. Hirschmann, K. R. Hanson, 'On Factoring Chirality and Stereoisomerism', Topics Stereochem. 1983, 14, 183-229.
20. H.-O. Kalinowski, H. Kessler, 'Fast Isomerizations about Double Bonds', Topics Stereochem. 1973, 7, 295-383.
21. M. Oki, 'Recent Advances in Atropisomerism', Topics Stereochem. 1983, 14, 1-81.
22. D. Casarini, M. Mancinelli, A. Mazzanti, F. Boschi, 'Stereodynamics and Absolute Configuration of Stereolabile Atropisomers in 2,2-Dimethyl-1-aryl-1- indanols', Chirality 2011, 23, 768-778.
23. M. Jung, M. Fluck, V. Schurig, 'Enantiomerization of 2,2'- Diisopropylbiphenyl during Chiral Inclusion Gas Chromatography: Determination of the Rotational Energy Barrier by Computer Simulation of Dynamic Chromatographic Elution Profiles', Chirality 1994, 6, 510-512.
24. V. Schurig, S. Reich, 'Determination of the Rotational Barriers of Atropisomeric Polychlorinated Biphenyls (PCBs) by a Novel Stopped-Flow Multidimensional GC Technique', Chirality 1998, 10, 316-320.
25. O. Trapp, G. Schoetz, V. Schurig, 'Determination of Enantiomerization Barriers by Dynamic and Stopped-Flow Chromatographic Methods', Chirality 2001, 13, 403-414.
26. O. Trapp, 'Fast and Precise Access to Enantiomerization Rate Constants in Dynamic Chromatography', Chirality 2006, 18, 489-497.
27. A. Ciogli, W. Bicker, W. Lindner, 'Determination of Enantiomerization Barriers of Hypericin and Pseudohypericin by Dynamic HPLC on Immobilized Polysaccharide-Type Chiral Stationary Phases and Off-Column Racemization Experiments', Chirality 2010, 22, 463-471.
28. P. L. Polavarapu, N. Jeirath, T. Kurtán, G. Pescitelli, K. Krohn, 'Determination of the Absolute Configurations at Stereogenic Centers in the Presence of Axial Chirality', Chirality 2009, 21, E202-E207.
29. T. B. Freedman, X. Cao, R. V. Olivera, Q. B. Cass, L. A. Nafie, 'Determination of the Absolute Configuration and Solution Conformation of Gossypol by Vibrational Circular Dichroism', Chirality 2003, 15, 196-200.
30. Q. B. Cass, A. L. Bassi, S. A. Matlin, 'First Direct Resolution of Gossypol Enantiomers on a Chiral HPLC Phase', Chirality 1999, 11, 46-49.
31. J. W. Jaroszewski, T. Strøm-Hansen, L. Lingaard Hansen, 'Optical Stability of Gossypol', Chirality 1992, 4, 216-221.
32. R. J. Friary, M. Spangler, R. Osterman, L. Schulman, J. H. Schwerdt, 'Enantiomerization of an Atropisomeric Drug', Chirality 1996, 8, 364-371.
33. F. C. Tucci, T. Hu, M. F. Mesleh, A. Bokser, E. Allsopp, T. D. Gross, Z. Guo, Y.-F. Zhu, R. S. Struthers, N. Ling, C. Chen, 'Atropisomeric Property of 1-(2,6-Difluorobenzyl)-3-[(2R)-amino-2-phenethyl]-5-(2-fluoro-3-methoxyphenyl) -6-methyluracil', Chirality 2005, 17, 559-564.
34. Y. S. Zhou, L. K. Tay, D. Hughes, S. Donahue, 'Simulation of the Impact of Atropisomer Interconversion on Plasma Exposure of Atropisomers of an Endothelin Receptor Antagonist', J. Clin. Pharmacol. 2004, 44, 680-688.
35. G. L. Lemière, F. C. Alderweireldt, 'Proposition for a New Definition of the Chiral Plane and Its Consequences for the Specification of Chirality', J. Org. Chem. 1980, 45, 4175-4179.
36. http://en.wikipedia.org/wiki/Helix.
37. R. H. Janke, G. Haufe, E.-U. Würthwein, J. H. Borkent, 'Racemization Barriers of Helicenes: A Computational Study', J. Am. Chem. Soc. 1996, 118, 6031-6035.
38. J.-L. Schmitt, A.-M. Stadler, N. Kyritsakas, J.-M. Lehn, 'Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features', Helv. Chim. Acta 2003, 86, 1598-1624.
39. http://en.wikipedia.org/wiki/Foldamer.
40. M. Goodman, A. S. Verdini, N. S. Choi, Y. Masuda, 'Polypeptide Stereochemistry', Topics Stereochem. 1970, 5, 69-166.
41. M. Farina, 'The Stereochemistry of Linear Macromolecules', Topics Stereochem. 1987, 17, 1-111.
42. C. De Rosa, 'Chain Conformation, Crystal Structures, and Structural Disorder in Stereoregular Polymers', Topics Stereochem. 2003, 24, 71-155.
43. http://en.wikipedia.org/wiki/Protein.
44. A. Toth, http://en.wikipedia.org/wiki/File:Myoglobin.png.
45. http://en.wikipedia.org/wiki/Protein-secondary
46. http://en.wikipedia.org/wiki/DNA; R. Wheeler, http://en.wikipedia.org/ wiki/File:A-DNA, B-DNA and Z-DNA.png.
47. J. K. Barton, 'Recognizing DNA Structures', Chem. Eng. News 1988, 66(39), 30-42
48. R. Orwant, 'Helix Heresy', New Sci. 2004, 182(2442), 38-41.
49. S. O. Kelley, J. K. Barton, 'Electron Transfer between Bases in Double Helical DNA', Science 1999, 283, 375-381.
50. E. J. Merino, A. K. Boal, J. K. Barton, 'Biological Contexts for DNA Charge Transport Chemistry', Curr. Opin. Chem. Biol. 2008, 12, 229-237.
51. D. D'Alonzo, A. Guaragna, G. Palumbo, 'Exploring the Role of Chirality in Nucleic Acid Recognition', Chem. Biodiversity 2011, 8, 373-413;
52. R. Corradini, S. Sforza, T. Tedeschi, R. Marchelli, 'Chirality as a Tool in Nucleic Acid Recognition: Principles and Relevance in Biotechnology and in Medicinal Chemistry', Chirality 2008, 19, 269-294.
53. J. E. Blackwood, C. L. Gladys, K. L. Loening, A. E. Petrarca, J. E. Rush, 'Unambiguous Specification of Stereoisomerism about Double Bonds', J. Am. Chem. Soc. 1968, 90, 509-510.
54. S. Fujita, 'Group-Theoretical Discussion on the E/Z-Nomenclature for Ethylene Derivatives. Discrimination between RS-Stereoisomeric Groups and Stereoisomeric Groups', J. Chem. Inf. Comput. Sci. 2004, 44, 1719-1726.
55. H. Kessler, 'Thermal Isomerization about Double Bonds. Rotation and Inversion', Tetrahedron 1974, 30, 1861-1870.
56. N. D. Epiotis, B. Bjorkquist, L. Bjorkquist, S. Sarkanen, 'Attractive Nonbonded Interactions in 1-Substituted Propenes. Consequences for Geometric and Conformational Isomerism', J. Am. Chem. Soc. 1973, 95, 7558-7562.
57. K. Bertsch, G. Karich, J. C. Jochims, 'Barriers to Hindered Rotation around the Double Bond System of Cumulenes (German)', Chem. Ber. 1977, 110, 3304-3313.
58. J. Sandström, 'Static and Dynamic Stereochemistry of Push-Pull and Strained Ethylenes', Topics Stereochem. 1983, 14, 83-181.
59. K. B. Wiberg, Y.-G. Wang, G. A. Petersson, W. F. Bailey, 'Intramolecular Nonbonded Attractive Interactions: 1-Substituted Propenes', J. Chem. Theory Comput. 2009, 5, 1033-1037.
60. C. C. Levin, R. Hoffmann, 'Role of Torsion in the Chirality of Twisted Olefins', J. Am. Chem. Soc. 1972, 94, 3446-3449.
61. A. F. Drakl, S. F. Mason, 'The Absorption and Circular Dichroism Spectra of Chiral Olefins', Tetrahedron 1977, 33, 937-949.
62. W. Luef, R. Keese, 'Strained Olefins: Structure and Reactivity of Nonplanar Carbon-Carbon Double Bonds', Topics Stereochem. 1991, 20, 231-318.
63. 3,8]dec-4-ene (Twistene)', Tetrahedron Lett. 1969, 10, 4609-4613.
64. W. Klyne, J. Buckingham, 'Atlas of Stereochemistry-Absolute Configurations of Organic Molecules', Chapman and Hall, London, 1974.
65. J. Bjørgo, D. R. Boyd, D. C. Neill, W. B. Jennings, 'Dynamic Stereochemistry of Imines and Derivatives. Part 11. Synthesis and Stereochemistry of (E)- and (Z)-Nitrones', J. Chem. Soc., Perkin Trans. 1 1977, 254-259.
66. J. Bjørgo, D. R. Boyd, C. G. Watson, W. B. Jennings, 'Equilibrium Distribution of E-Z-Ketimine Isomers', J. Chem. Soc., Perkin Trans. 2 1974, 757-762.