Stereoselective palladium-catalyzed α-arylation of 3-aryl-1-indanones: An asymmetric synthesis of (+)-pauciflorol F

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6611-6618

  Lee, Bong Hyang ^a,b   Choi, Young Lok ^a,c   Shin, Seunghoon ^b   Heo, Jung Nyoung ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Hanyang University   (South Korea)

^c Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYLATION REACTIONS; ARYLATIONS; ASYMMETRIC SYNTHESIS; STEREO-SELECTIVE;

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CATALYSIS; SODIUM;

STEREOSELECTIVITY;

1 (3,5 DIMETHOXYPHENYL) 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1,3 BIS(3,5 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 2 (4 METHOXYPHENYL) 3 PHENYL 1H INDEN 1 ONE; 2 HYDROXY 2 (4 METHOXYPHENYL) 3 PHENYL 2,3 DIHYDRO 1H INDEN 1 ONE; 3 (3,5 DIMETHOXYPHENYL) 2 HYDROXY 4,6 DIMETHOXY 2 (4 METHOXYPHENYL) 2,3 DIHYDRO 1H INDEN 1 ONE; 3 (3,5 DIMETHOXYPHENYL) 4,6 DIMETHOXY 2 (4 METHOXYPHENYL) 2,3 DIHYDRO 1H INDEN 1 ONE; 3 (3,5 DIMETHOXYPHENYL) 4,6 DIMETHOXY 2 PHENYL 2,3 DIHYDRO 1H INDEN 1 ONE; 3 (3,5 DIMETHOXYPHENYL) 4,6 DIMETHOXY 2,3 DIHYDRO 1H INDEN 1 ONE; 3 ARYL 1 INDANONE; 4 BROMOANISOLE; 4,6 DIMETHOXY 3 (4 METHOXYPHENYL) 2,3 DIHYDRO 1H INDEN 1 ONE; ANISOLE DERIVATIVE; INDANONE DERIVATIVE; PALLADIUM; PAUCIFLOROL F; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEMETHYLATION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CATALYSIS; HYDROCARBONS, BROMINATED; INDANS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; STILBENES;

EID: 80051758049     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2009164     Document Type: Article

References (44)

1. Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002; Vols. 1 and 2.
2. Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082-1146
3. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676-707
4. Heo, J.-N.; Song, Y. S.; Kim, B. T. Tetrahedron Lett. 2005, 46, 4621-4625
5. Song, Y. S.; Lee, Y.-J.; Kim, B. T.; Heo, J.-N. Tetrahedron Lett. 2006, 47, 7427-7430
6. Kim, Y. H.; Lee, H.; Kim, Y. J.; Kim, B. T.; Heo, J.-N. J. Org. Chem. 2008, 73, 495-501
7. Kim, J. K.; Kim, Y. H.; Nam, H. T.; Kim, B. T.; Heo, J.-N. Org. Lett. 2008, 10, 3543-3546
8. Choi, Y. L.; Yu, C.-M.; Kim, B. T.; Heo, J.-N. J. Org. Chem. 2009, 74, 3948-3951
9. Goh, Y.-H.; Kim, G.; Kim, B. T.; Heo, J.-N. Heterocycles 2010, 80, 669-677
10. Choi, Y. L.; Lee, H.; Kim, B. T.; Choi, K.; Heo, J.-N. Adv. Synth. Catal. 2010, 352, 2041-2049
11. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109
12. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383
13. Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740-1742
14. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370
15. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195-200
16. Chan, G.; Kwong, F. Y.; Chan, H. O.; Yu, W.-Y.; Chan, A. S. C. Chem. Commun. 2006, 1413-1415
17. Conrad, J. C.; Kong, J.; Laforteza, B. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 11640-11641
18. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W. W.; Fong, H. H. S.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218-220
19. Ito, T.; Tanaka, T.; Iinuma, M.; Nakaya, K.-i.; Takahashi, Y.; Sawa, R.; Murata, J.; Darnaedi, D. J. Nat. Prod. 2004, 67, 932-937
20. Adesanya, S. A.; Nia, R.; Martin, M.-T.; Boukamcha, N.; Montagnac, A.; Pais, M. J. Nat. Prod. 1999, 62, 1694-1695
21. Li, W.; Li, H.; Li, Y.; Hou, Z. Angew. Chem., Int. Ed. 2006, 45, 7609-7611
22. Tanaka, T.; Iinuma, M.; Murata, H. Phytochemistry 1998, 48, 1045-1049
23. Kim, H. J.; Saleem, M.; Seo, S. H.; Jin, C.; Lee, Y. S. Planta Med. 2005, 71, 973-976
24. Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1995, 38, 4821-4829
25. Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447
26. deSolms, S. J.; Woltersdorf, O. W., Jr.; Cragoe, E. J., Jr. J. Med. Chem. 1978, 21, 437-443
27. Ahn, J. H.; Shin, M. S.; Jung, S. H.; Kang, S. K.; Kim, K. R.; Rhee, S. D.; Jung, W. H.; Yang, S. D.; Kim, S. J.; Woo, J. R.; Lee, J. H.; Cheon, H. G.; Kim, S. S. J. Med. Chem. 2006, 49, 4781-4784
28. Bo, C.; Lu, J.-P.; Xie, X.-G.; She, X.-G.; Pan, X.-F. Chin. J. Org. Chem. 2006, 26, 1300-1302
29. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753-1765
30. Snyder, S. A.; Zografos, A. L.; Lin, Y. Angew. Chem., Int. Ed. 2007, 46, 8186-8191
31. Jeffrey, J. L.; Sarpong, R. Org. Lett. 2009, 11, 5450-5453
32. Yang, Y.; Philips, D.; Pan, S. J. Org. Chem. 2011, 76, 1902-1905
33. Seery, M. K.; Draper, S. M.; Kelly, J. M.; McCabe, T.; McMurry, T. B. H. Synthesis 2005, 470-474
34. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370
35. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819
36. Alesso, E. N.; Finkielsztein, L. M.; Lantaño, B.; Bianchi, D. E.; Moltrasio Iglesias, G. Y.; Aguirre, J. M. Aust. J. Chem. 1997, 50, 149-152
37. Marco, J. L. Synth. Commun. 1996, 26, 4225-4231
38. Verbel, J.; Carrie, R. Bull. Soc. Chim. Fr. 1982, 2, 116-124
39. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245
40. Srebnik, M.; Mechoulam, R.; Yona, I. J. Chem. Soc., Perkin Trans. I 1987, 1423-1427
41. Clark, W. M.; Kassick, A. J.; Plotkin, M. A.; Eldridge, A. M.; Lantos, I. Org. Lett. 1999, 1, 1839-1842
42. Clark, W. M.; Tickner-Eldridge, A. M.; Huang, G. K.; Pridgen, L. N.; Olsen, M. A.; Mills, R. J.; Lantos, I.; Baine, N. H. J. Am. Chem. Soc. 1998, 120, 4550-4551
43. Manning, C.; McClory, M. R.; McCullough, J. J. J. Org. Chem. 1981, 46, 919-930
44. Saito, A.; Umakoshi, M.; Yagyu, N.; Hanzawa, Y. Org. Lett. 2008, 10, 1783-1785