Enantioselective chromatographic resolution and one-pot synthesis of enantiomerically pure sulfoxides over a homochiral Zn-organic framework

Journal of the American Chemical Society

Volumn 129, Issue 43, 2007, Pages 12958-12959

  Nuzhdin, Alexey L ^a   Dybtsev, Danil N ^b   Bryliakov, Konstantin P ^a   Talsi, Evgenii P ^a   Fedin, Vladimir P ^b  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b NIKOLAEV INSTITUTE OF INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE; SULFOXIDE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; CONCEPTUAL FRAMEWORK; ENANTIOSELECTIVITY; LIQUID CHROMATOGRAPHY; METAL ORGANIC FRAMEWORK; OXIDATION; PRODUCT RECOVERY; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 35848970318     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076276p     Document Type: Article

References (25)

1. (a) Noro, S.; Kitagawa, S.; Kondo, M.; Seki, K. Angew. Chem., Int. Ed. 2000, 39, 2081-2084.
2. (b) Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Science 2002, 295, 469.
3. (c) Chun, H.; Dybtsev, D. N.; Kim, H.; Kim, K. Chem. Eur. J. 2005, 11, 3521-3529.
4. (d) Matsuda, R.; Kitaura, R.; Kitagawa, S.; Kubota, Y.; Belosludov, R. V.; Kobayashi, T. C.; Sakamoto, H.; Chiba, T.; Takata, M.; Kawazoe, Y.; Mita, Y. Nature 2005, 436, 238-241.
5. (e) Zhao, X.; Xiao, X.; Fletcher, A. J.; Thomas, K. M.; Bradshaw, D.; Rosseinsky, M. J. Science 2004, 306, 1012-1015.
6. (f) Férey, G.; Serre, C.; Mellot-Draznieks, C.; Millange, F.; Surblé, S.; Dutour, J.; Margiolaki, I. Angew. Chem., Int. Ed. 2004, 43, 6296-6301.
7. (g) Wong-Foy, A. G.; Matzger, A. J.; Yaghi, O. M. J. Am. Chem. Soc. 2006, 128, 3494.
8. (a) Seo, J. S.; Wand, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y.; Kim, K. Nature 2004, 404, 982-986.
9. (b) Maji, T. K.; Uemura, K.; Chang, H.-C.; Matsuda, R.; Kitagawa, S. Angew. Chem., Int. Ed. 2004, 43, 3269-3272.
10. (c) Dybtsev, D. N.; Chun, H.; Yoon, S. H.; Kim, D.; Kim, K. J. Am. Chem. Soc. 2004, 126, 32-33.
11. (d) Bradshaw, D.; Prior, T. J.; Cussen, E. J.; Claridge, J. B.; Rosseinsky, M. J. J. Am. Chem. Soc. 2004, 126, 6106-6114.
12. (e) Xiong, R.-G.; You, X.-Z.; Abrahams, B. F.; Xue, Z.; Che, C.-M. Angew. Chem., Int. Ed. 2001, 40, 4422-4425.
13. (f) Wu, C.-D.; Hu, A.; Zhang, L.; Lin, W. J. Am. Chem. Soc. 2005, 127, 8940.
14. (a) Evans, O. R.; Ngo, H. L.; Lin, W. J. Am. Chem. Soc. 2001, 123, 10395-10396.
15. (b) Song, Y.-M.; Zhou, T.; Wang, X.-S.; Li, X.-N.; Xiong, R.-G. Cryst. Growth Des. 2006, 6, 14-17.
16. (c) Xie, Y.-R.; Wang, X.-S.; Zhao, H.; Zhang, J.; Weng, L.-H.; Duan, C.-Y.; Xiong, R.-G.; You, X.-Z.; Xue, Z.-L. Organometallics 2003, 22, 4396-4398.
17. (d) Ye, Q.; Wang, X.-S.; Zhao, H.; Xiong, R.-G. Chem. Soc. Rev. 2005, 34, 208-225.
18. (e) Cavallo, L.; Cucciolito, M. E.; De Martino, A.; Giordano, F.; Orabona, I.; Vitagliano, A. Chem. Eur. J. 2000, 6, 1127-1139.
19. (a) Dybtsev, D. N.; Nuzhdin, A. L.; Chun, H.; Bryliakov, K. P.; Talsi, E. P.; Fedin, V. P.; Kim, K. Angew. Chem., Int. Ed. 2006, 45, 916-920.
20. (b) Xiong, R.-G.; Zuo, J. L.; You, X. Z.; Fun, H. K.; Raj, S. S. S. New. J. Chem. 1999, 23, 1051-1052.
21. 2Ph) cannot enter the pores and hence display zero sorption.
22. (a) Alienmark, S. G. Chromatographic Enantioseparations; Ellis Horwood: Chichester, U.K., 1988.
23. (b) Chankvetadze, B.; Yamamoto, C.; Okamoto, Y. J. Chromatogr. A 2001, 922, 127-137.
24. (c) Berthod, A.; Xiao, T. L.; Liu, Y.; Jenks, W. S.; Armstrong, D. W. J. Chromatogr. A 2002, 955, 53-69.
25. (d) Cass, Q. B.; Batigalhia, F. J. Chromatogr. A 2003, 987, 445-452.