Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary amine–thiourea: Synthesis of modified chromanes with anticancer potency

Chemical Communications

Volumn 48, Issue 3, 2012, Pages 446-448

  Jiang, Xianxing ^a,b   Wu, Lipeng ^a   Xing, Yanhong ^a   Wang, Long ^a   Wang, Shoulei ^a   Chen, Zongyao ^a   Wang, Rui ^a,b  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMAN DERIVATIVE; ROSIN; THIOUREA DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; IC 50;

EID: 82955165738     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc14379d     Document Type: Article

References (26)

1. G. P. Ellis and I. M. Lockhart in Chromans and Tocopherols, Wiley-Interscience, New York, 1981
2. E. E. Schweizer and O. Meeder-Nycz, in Chromenes, Chromanes, Chromones, ed. G. P. Ellis, Wiley-Interscience, New York, 1977, pp. 11-139
3. R. Hiessböck, C. Wolf, E. Richter, M. Hitzler, P. Chiba, M. Kratzel, G. Ecker, J. Med. Chem., 1999, 42, 1921.
4. C. A. Lipinski, C. E. Aldinger, T. A. Beyer, J. Bordner, D. F. Burdi, D. L. Bussolotti, P. B. Inskeep, T. W. Siegel, J. Med. Chem., 1992, 35, 2169.
5. N. Cohen, G. Weber, B. L. Banner, R. J. Lopresti, B. Schaer, A. Focella, G. B. Zenchoff, A. Chiu, L. Todaro, M. O'Donnell, A. F. Welton, D. Brown, R. Garippa, H. Crowley, D. W. Morgan, J. Med. Chem., 1989, 32, 1842.
6. G. W. Burton, K. U. Ingold, Acc. Chem. Res., 1986, 19, 194.
7. A. G. Doyle, E. N. Jacobsen, Chem. Rev., 2007, 107, 5713.
8. S. J. Connon, Chem.-Eur. J., 2006, 12, 5418.
9. M. S. Taylor, E. N. Jacobsen, Angew. Chem., Int. Ed., 2006, 45, 1520.
10. Y. Takemoto, Org. Biomol. Chem., 2005, 3, 4299.
11. X. X. Jiang, Y. F. Zhang, A. S. C. Chan, R. Wang, Org. Lett., 2009, 11, 153.
12. X. X. Jiang, Y. M. Cao, Y. Q. Wang, L. P. Liu, F. F. Shen, R. Wang, J. Am. Chem. Soc., 2010, 132, 15328.
13. X. X. Jiang, D. Fu, G. Zhang, Y. M. Cao, L. P. Liu, R. Wang, Chem. Commun., 2010, 46, 4294.
14. X. X. Jiang, G. Zhang, D. Fu, Y. M. Cao, F. F. Shen, R. Wang, Org. Lett., 2010, 12, 1544.
15. X. X. Jiang, Y. F. Zhang, X. Liu, G. Zhang, L. H. Lai, L. P. Wu, J. N. Zhang, R. Wang, J. Org. Chem., 2009, 74, 5562.
16. Z. Xu, L. Liu, K. Wheeler, H. Wang, Angew. Chem., Int. Ed., 2011, 50, 3484.
17. F. Gallier, H. Hussain, A. Martel, A. Kirschning, G. Dujardin, Org. Lett., 2009, 11, 3060.
18. R. P. Herrera, D. Monge, E. Martin-Zamora, R. Fernández, J. M. Lassaletta, Org. Lett., 2007, 9, 3303.
19. G. Gaulon, R. Dhal, T. Chapin, V. Maisonneuve, G. Dujardin, J. Org. Chem., 2004, 69, 4192.
20. K. Juhl, K. A. Jørgensen, Angew. Chem., Int. Ed., 2003, 42, 1498.
21. A. Arboré, G. Dujardin, C. Maignan, Eur. J. Org. Chem., 2003, 4118.
22. N. Halland, T. Velgaard, K. A. Jørgensen, J. Org. Chem., 2003, 68, 5067.
23. T. B. Poulsen, K. A. Jørgensen, Chem. Rev., 2008, 108, 2903.
24. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett, 2005, 1199.
25. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem., Int. Ed., 2004, 43, 550.
26. K. A. Jørgensen, Synthesis, 2003, 1117.