New sterically driven mode for generation of helical chirality

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1797-1800

  Ueki, Hisanori ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

AMIDES; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 65249106731     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900357d     Document Type: Article

References (41)

1. Watson, D.; Crick. F. C. H. Nature (London) 1953, 171, 737-738.
2. Gotto. A. M.; Shore, B. Nature (London) 1969, 224, 69-70.
3. (a) Kellogg, G. J.; Walton. D. G.; Mayes, A. M.; Lamboov, P.; Russell. T. P.; Gallagher, P. D.: Satija, S. K. Phys. Rev. Lett. 1996, 76, 2503-2506.
4. (b) Lambooy, P.; Russell, T. P.; Kellogg. G. J.; Maves, A. M.; Gallagher, P. D.; Satija, S. K. Phys Rev. Lett. 1994, 72, 2899-2902.
5. (c) Maritan, A.; Micheletti, C; Trovato, A.; Banavar, J. P. Nature (London) 2000, 406, 287-290.
6. (d) Zhu, S.; Liu, Y.; Rafailovich, M. H.; Sokolov, J.; Gersappe, D.; Winesett. D. A.; Ade, H. Nature (London) 1999, 400, 49- 51.
7. Snir, Y.; Kamien, R. D. Science 2005, 307. 1067,
8. (a) Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68.
9. (b) Piguet, C; Bernardmelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062.
10. (c) Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Veciana, J. ~Adv. Mater. 1998, 10, 1001-1005.
11. (d) Cornelissen. J. J. L. H.; Fischer, M.; Sommerdijk. N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427- 1430.
12. (e) Soloshonok, V. A.; Ueki, H. J. Am. Chem. Soc. 2007, 129, 2426- 2427.
13. (f) Soloshonok, V. A.; Ueki, H.; Moore, J. L.; Ellis. T. K. J. Am. Chem. Soc. 2007, 129, 3512-3513.
14. (g) Ito, H.; Furasho, Y.; Hasegawa, T.; Yashima, E. J. Am. Chem. Soc. 2008, 130, 14008-14015.
15. (h) Kawauchi, T.; Kitaura, A.; Kumaki, J.; Kusanagi, H.; Yashima, E. J. Am. Chem. Soc. 2008, 130, 11889-11891.
16. (i) Yashima. E.; Maeda, K.; Furusho. Y. Acc. Chem. Res. 2008, 41, 1166-1180,
17. Via ap-chromatography:(a) Soloshonok. V. A. Angew. Chem., Int. Ed 2006, 45, 766-769.
18. (b) Soloshonok, V. A.; Berbasov, D. O. J. Fluor. Chem. 2006, 127, 597-603.
19. (c) Soloshonok. V. A.; Berbasov, D. O. Chim. Oggi/Chem. Today 2006, 24, 44-47.
20. Via sublimation:Soloshonok, V. A.; Ueki, H; Yasumoto, M; Mekala, S.: Hirschi. J. S.: Singleton. D. A J. Am. Chem. Soc. 2007, 129. 12112- 12113.
21. (a) Bravo, P.; Farina, A.; Kukhar, V. P.; Markovsky, A. L.; Meille, S. V.; Soloshonok, V. A.; Sorochinsky. A. E.; Viani, F.; Zanda. M. J. Org. Chem. 1997, 62, 3424-3425.
22. (b) Soloshonok. V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima. N. J. Org. Chem. 1997, 62, 3470- 3479.
23. (c) Soloshonok, V. A.; Gems, 1.1.; Yagupolskii, Y. L.; Kukhar, V. P. Zh. Org. Khim. 1987, 23, 2308-2313.
24. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550.
25. (e) Soloshonok, V. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245-254.
26. (a) Soloshonok, V. A.; Kirilenko. A. G.; Kukhar. V. P.; Resnati. G. Tetrahedron Lett. 1993, 34, 3621-3624.
27. (b) Bravo, P.; Farina, A.; Frigerio, M.; Valdo Meille, S.; Viani, F.; Soloshonok. V. A. Tetrahedron: Asymmetry 1994, 5, 987-1004.
28. (c) Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1997, 53, 8307-8314.
29. (d) Soloshonok, V. A.; Avilov, D. V.; Kukhar. V. P.; Tararov, V. 1.; Saveleva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon, Y. N. Tetrahedron: Asymmetry 1995, 6. 1741- 1756.
30. (a) Metrangolo, P.; Mever, R; Pilafi, T.: Resnati, G.; Terraneo. G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127.
31. (b) Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356.
32. (c) Zaworotko, M. J. Angew. Chem., Int Ed. 1998, 37, 1211-1213,
33. Lait, S. M.: Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 2003, 14, 749-756.
34. Duda, L.; Erker. G.; Fröhlieh, R.: Zippel, F. Eur. J. Inorg. Chem. 1998, 1153-1162.
35. For example:(a) Ananda, K.; Aravinda, S.; Vasudev, P. G.; Raja, K. M. P.; Sivaramakrishnan, H.; Nagarajan, K.; Shamala, N.; Balaram, P. Curt: Sci. 2003, 85, 1002.
36. (b) Belokon, Y. N.; Bespalova, N. B.; Churkina, T. D.; Cisarova, L; Ezernitskaya, M. G.; Harutyunyan, S. R.; Hrdina, R.; Kagan, H. B.; Kocovsky, K. A.; Kochetkov, K. A.; Larionov, O. V.; Lyssenko, K. A.; North, M.; Polasek, M.; Peregudov, A. S.; Prisyazhnyuk, V. V.; Vyskoctl, S. J. Am Chem. Soc. 2003, 125, 12860.
37. (c) Das, A. K.; Bose, P. P.; Drew, M. G. B.; Banerjee, A. Tetrahedron 2007, 63, 7432.
38. For example:(a) Aravinda, S.; Ananda, K.; Shamala, N.; Balaram, P. Chem.-Eur. J. 2003, 9, 4789.
39. (b) Drew, M. G. B.; Hill, C; Hudson, M. J.; Iveson. P. B.; Madic, C; Youngs. T. G. A. Dalton Trans. 2004, 244.
40. For example:(a) Aubry, A.; Vitoux, B.; Marraud, M. Cryst. Struct. Commun. 1982, 11. 135.
41. (b) Itai, A.; Toriumi, Y.: Saito, S.: Kagechika. H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10694.