Optical resolution of chiral buckybowls by chiral HPLC

Chemistry Letters

Volumn 39, Issue 6, 2010, Pages 646-647

  Tsuruoka, Ryoji ^a   Higashibayashi, Shuhei ^a   Ishikawa, Takeharu ^b   Toyota, Shinji ^b   Sakurai, Hidehiro ^a,c  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77952730113     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.646     Document Type: Article

References (33)

1. For recent reviews: a) Y.-T. Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843.
2. b) V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868.
3. A. Sygula, P. W. Rabideau, in Carbon-Rich Compounds, ed. by M. M. Haley, R. R. Tykwinski, Wiley-VCH, Weinheim, Germany, 2006, pp. 529-565.
4. 3 symmetric chiral buckybowls, see: a) A. H. Abdourazak, Z. Marcinow, A. Sygula, R. Sygula, P. W. Rabideau, J. Am. Chem. Soc. 1995, 117, 6410.
5. b) S. Hagen, M. S. Bratcher, M. S. Erickson, G. Zimmermann, L. T. Scott, Angew. Chem., Int. Ed. Engl. 1997, 36, 406.
6. T. Amaya, T. Nakata, T. Hirao, J. Am. Chem. Soc. 2009, 131, 10810. For racemic synthesis of corannulene derivatives, see ref 1 and following references:
7. L. T. Scott, M. M. Hashemi, M. S. Bratcher, J. Am. Chem. Soc. 1992, 114, 1920.
8. e) V. M. Tsefrikas, S. Arns, P. M. Merner, C. C. Warford, B. L. Merner, L. T. Scott, G. J. Bodwell, Org. Lett. 2006, 8, 5195.
9. f) Y.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870.
10. For nomenclature of chiral buckybowls, see Supporting Information and ref 4. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/joumals/chem-lett/index .html.
11. S. Higashibayashi, H. Sakurai, J. Am. Chem. Soc. 2008, 130, 8592.
12. a) C. Thilgen, F. Diederich, Chem. Rev. 2006, 106, 5049.
13. b) X. Peng, N. Komatsu, S. Bhattacharya, T. Shimawaki, S. Aonuma, T. Kimura, A. Osuka, Nat. Nanotechnol. 2007, 2, 361, and references cited therein.
14. H. Sakurai, T. Daiko, H. Sakane, T. Amaya, T. Hirao, J. Am. Chem. Soc. 2005, 127, 11580.
15. -1 ).
16. Longer reaction time (2 h) gave lower yield (16%) possibly owing to overreactions.
17. See Supporting Information.
18. For experimental studies for corannulenes, see ref 2d and following references: a) A. Sygula, A. H. Abdourazak, P. W. Rabideau, J. Am. Chem. Soc. 1996, 118, 339.
19. b) Z. Marcinow, A. Sygula, A. Ellern, P. W. Rabideau, Org. Lett. 2001, 3, 3527.
20. T. J. Seiders, K. K. Baldridge, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc 2001, 123, 517.
21. T. Hayama, K. K. Baldridge, Y.-T. Wu, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2008, 130, 1583. For sumanenes, see:
22. e) H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878.
23. f) T. Amaya, H. Sakane, T. Muneishi, T. Hirao, Chem. Commun. 2008, 765.
24. For theoretical studies, see: a) G. J. Gleicher, Tetrahedron 1967, 23, 4257.
25. b) J. Kao, J. Am. Chem. Soc. 1987, 109, 3817.
26. A. Borchardt, A. Fuchicello, K. V. Kilway, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 1921.
27. R. L. Disch, J. M. Schulman, J. Am. Chem. Soc. 1994, 116, 1533.
28. e) A. Sygula, P. W. Rabideau, J. Chem. Soc., Chem. Commun. 1994, 1497.
29. f) S. Hagen, H. Christoph, G. Zimmermann, Tetrahedron 1995, 51, 6961,
30. g) P. U. Biedermann, S. Pogodin, I. Agranat, J. Org. Chem. 1999, 64, 3655.
31. h) T. C. Dinadayalane, U. D. Priyakumar, G. N. Sastry, THEOCHEM 2001, 543, 1.
32. T. C. Dinadayalane, G. N. Sastry, J. Org. Chem. 2002, 67, 4605.
33. j) T. C. Dinadayalane, S. Deepa, A. S. Reddy, G. N. Sastry, J. Org. Chem. 2004, 69, 8111.