Enantioselective synthesis of triarylmethanes by chiral imidodiphosphoric acids catalyzed friedel-crafts reactions

Organic Letters

Volumn 16, Issue 4, 2014, Pages 1096-1099

  Zhuo, Ming Hua ^a   Jiang, Yi Jun ^a   Fan, Yan Sen ^a   Gao, Yang ^a   Liu, Song ^a   Zhang, Suoqin ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; DRUG DERIVATIVE; IMIDODIPHOSPHONIC ACID; INDOLE DERIVATIVE; METHANE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CATALYSIS; DIPHOSPHONATES; INDOLES; METHANE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84894524215     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403680c     Document Type: Article

References (50)

1. Duxbury, D. F. Chem. Rev. 1993, 93, 381
2. Shchepinov, M. S.; Korshun, V. A. Chem. Soc. Rev. 2003, 32, 170
3. Nair, V.; Thomas, S.; Mathew, S. C.; Abhilash, K. G. Tetrahedron 2006, 62, 6731
4. Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250
5. Bossche, H. V.; Willemsens, G.; Roels, I.; Bellens, D.; Moereels, H.; Coene, M.-C.; Jeune, L. L.; Lauwers, W.; Janssen, P. A. Biochem. Pharmacol. 1990, 40, 1707
6. Recanatini, M.; Cavalli, A.; Valenti, P. Med. Res. Rev. 2002, 22, 282
7. Wood, P. M.; Woo, L. L.; Labrosse, J.-R.; Trusselle, M. N.; Abbate, S.; Longhi, G.; Castiglioni, E.; Lebon, F.; Purohit, A.; Reed, M. J. J. Med. Chem. 2008, 51, 4226
8. Takahashi, K.; Yamagishi, G.; Hiramatsu, T.; Hosoya, A.; Onoe, K.; Doi, H.; Nagata, H.; Wada, Y.; Onoe, H.; Watanabe, Y.; Hosoya, T. Bioorg. Med. Chem. 2011, 19, 1464
9. Wood, P. M.; Woo, L. W.; Thomas, M. P.; Mahon, M. F.; Purohit, A.; Potter, B. V. ChemMedChem 2011, 6, 1423
10. Cho, S. D.; Yoon, K.; Chintharlapalli, S.; Abdelrahim, M.; Lei, P.; Hamilton, S.; Khan, S.; Ramaiah, S. K.; Safe, S. Cancer Res. 2007, 67, 674
11. Inamoto, T.; Papineni, S.; Chintharlapalli, S.; Cho, S. D.; Safe, S.; Kamat, A. M. Mol. Cancer Ther. 2008, 7, 3825
12. Cho, S. D.; Lee, S. O.; Chintharlapalli, S.; Abdelrahim, M.; Khan, S.; Yoon, K.; Kamat, A. M.; Safe, S. Mol. Pharmacol. 2010, 77, 396
13. Yoon, K.; Lee, S. O.; Cho, S. D.; Kim, K.; Khan, S.; Safe, S. Carcinogenesis 2011, 32, 836
14. For thiophene containing triarylmethanes, see: Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289
15. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
16. Sun, F.-L.; Zheng, X.-J.; Gu, Q.; He, Q.-L.; You, S.-L. Eur. J. Org. Chem. 2010, 47
17. Taylor, B. L.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790
18. Harris, M. R.; Hanna, L. E.; Greene, M. A.; Moore, C. E.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 3303
19. Katritzky, A. R.; Toader, D. J. Org. Chem. 1997, 62, 4137
20. Esquivias, J.; Gómez Arrayás, R.; Carretero, J. C. Angew. Chem. 2006, 118, 645
21. He, Q.-L.; Sun, F.-L.; Zheng, X.-J.; You, S.-L. Synlett 2009, 1111
22. Thirupathi, P.; Kim, S. S. Tetrahedron 2010, 66, 2995
23. Thirupathi, P.; Kim, S. S. J. Org. Chem. 2010, 75, 5240
24. Wang, Y.; Ding, K.-L. Chin. J. Org. Chem. 2001, 21, 763
25. Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550
26. Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199
27. Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903
28. Sheng, Y.-F.; Zhang, A. J.; Zheng, X.-J.; You, S.-L. Chin. J. Org. Chem. 2008, 28, 605
29. You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190
30. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
31. You, S.-L.; Zeng, M. Synlett 2010, 1289
32. Čorić, I.; List, B. Nature 2012, 483, 315
33. Liao, S.; Čorić, I.; Wang, Q.; List, B. J. Am. Chem. Soc. 2012, 134, 10765
34. Kim, J. H.; Čorić, I.; Vellalath, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 4474
35. Chen, Y.-Y.; Jiang, Y.-J.; Fan, Y.-S.; Sha, D.; Wang, Q.; Zhang, G.; Zheng, L.; Zhang, S. Tetrahedron: Asymmetry 2012, 23, 904
36. Wu, K.; Jiang, Y. J.; Fan, Y. S.; Sha, D.; Zhang, S. Chem.-Eur. J. 2013, 19, 474
37. An, D.; Fan, Y.-S.; Gao, Y.; Zhu, Z.-Q.; Zheng, L.-Y.; Zhang, S. Eur. J. Org. Chem. 2014, 301
38. Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259
39. Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593
40. Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620
41. Sun, F.-L.; Zeng, M.; Gu, Q.; You, S.-L. Chem.-Eur. J. 2009, 15, 8709
42. Liang, T.; Zhang, Z.; Antilla, J. C. Angew. Chem., Int. Ed. 2010, 49, 9734
43. Rueping, M.; Uria, U.; Lin, M.-Y.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732
44. Wang, S.-G.; Han, L.; Zeng, M.; Sun, F.-L.; Zhang, W.; You, S.-L. Org. Biomol. Chem. 2012, 10, 3202
45. Song, L.; Guo, Q.-X.; Li, X.-C.; Tian, J.; Peng, Y.-G. Angew. Chem., Int. Ed. 2012, 51, 1899
46. Čorić, I.; Kim, J. H.; Vlaar, T.; Patil, M.; Thiel, W.; List, B. Angew. Chem., Int. Ed. 2013, 52, 3490
47. Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534
48. Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518
49. Pratihar, S.; Roy, S. J. Org. Chem. 2010, 75, 4957
50. CCDC 948305 (2b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambrige Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.