An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids

Journal of Organic Chemistry

Volumn 77, Issue 2, 2012, Pages 999-1009

  Chen, Jie ^a   Zhou, Ling ^a   Tan, Chong Kiat ^a   Yeung, Ying Yeung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; ENANTIOSELECTIVE; ENANTIOSELECTIVE APPROACH; GOOD YIELD; PHTHALIDES;

CARBOXYLIC ACIDS; STYRENE;

ENANTIOSELECTIVITY;

3 BROMO 3,4 DIHYDROISOCOUMARIN; 3,4 DIHYDROISOCOUMARIN; 4 BROMO 3 (3 CHLOROPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (3 METHYLPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (3 NITROPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (4 ACETOXYPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (4 CHLOROPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (4 FLUOROPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 (4 METHOXYPHENYL) 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3 [4 (TRIFLUOROMETHYL)PHENYL] 3,4 DIHYDROISOCHROMEN 1 ONE; 4 BROMO 3,4 DIHYDRO 3 (NAPHTHALEN 2 YL)ISOCHROMEN 1 ONE; 4 BROMO 3,4 DIHYDRO 3 4 TOLYLISOCHROMEN 1 ONE; 4 BROMO 3,4 DIHYDRO 3 PHENYLISOCHROMEN 1 ONE; 4 BROMO 3,4 DIHYDRO 5 METHYL 3 PHENYLISOCHROMEN 1 ONE; 4 BROMO 6 CHLORO 3,4 DIHYDRO 3 PHENYLISOCHROMEN 1 ONE; 4 BROMO 6 FLUORO 3,4 DIHYDRO 3 PHENYLISOCHROMEN 1 ONE; 4 BROMO 7 FLUORO 3,4 DIHYDRO 3 PHENYLISOCHROMEN 1 ONE; 4 N 3,4 DIHYDROISOCOUMARIN; 4 O 3,4 DIHYDROISOCOUMARIN; BENZOIC ACID; BROMINE; CARBOXYLIC ACID; ISOCOUMARIN DERIVATIVE; PHTHALIDE DERIVATIVE; STYRENE; THIOCARBAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BROMOCYCLIZATION; CATALYSIS; CYCLIZATION; DEBROMINATION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

CARBOXYLIC ACIDS; CHEMISTRY TECHNIQUES, SYNTHETIC; COUMARINS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; STYRENE;

EID: 84862907743     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202221c     Document Type: Article

References (71)

1. Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. 1999, 7, 1445-1450
2. Paraschos, S.; Magiatis, P.; Kalpoutzakis, E.; Harvala, C.; Skaltsounis, A.-L. J. Nat. Prod. 2001, 64, 1585-1587
3. Saeed, A. J. Asian Nat. Prod. Res. 2006, 8, 417-423
4. Zhang, H.; Matsuda, H.; Kumahara, A.; Ito, Y.; Nakamura, S.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2007, 17, 4972-4976
5. Li, Y.; Plitzko, I.; Zaugg, J.; Hering, S.; Hambuger, M. J. Nat. Prod. 2010, 73, 768-770
6. Haritakun, R.; Sappan, M.; Suvannakad, R.; Tasanathai, K.; Isaka, M. J. Nat. Prod. 2010, 73, 75-78
7. Xu, L.; He, Z.; Xue, J.; Chen, X.; Wei, X. J. Nat. Prod. 2010, 73, 885-889
8. Lehmann, F.; Currier, E. A.; Olsson, R.; Ma, J.-N.; Burstein, E. S.; Hacksell, U.; Luthman, K. Bioorg. Med. Chem. 2010, 18, 4844-4854
9. Adams, C.; Papillon, J.; Ksander, G. M. Patent WO 2007117982, 2007.
10. Endringer, D. C.; Guimaraes, K. G.; Kondratyuk, T. P.; Pezzuto, J. M.; Braga, F. C. J. Nat. Prod. 2008, 71, 1082-1084
11. Hobson, S. J.; Parkin, A.; Marquez, R. Org. Lett. 2008, 10, 2813-2816
12. Yang, J. X.; Chen, Y.; Huang, C.; Shu, Z.; Lin, Y. Chem. Nat. Compd. 2011, 47, 13-16
13. Egan, B. A.; Paradowski, M.; Thomas, L. H.; Marquez, R. Org. Lett. 2011, 13, 2086-2089
14. Dey, D.; Neogi, P.; Sen, A.; Sharma, S. D.; Nag, B. Patent WO 02/30888 A2, 2002.
15. Fitzgerald, J. J.; Pagano, A. R.; Sakoda, V. M.; Olofson, R. A. J. Org. Chem. 1994, 59, 4117-4121
16. Hentemann, M. F.; Allen, J. G.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 1937-1940
17. Suzuki, T.; Yamada, T.; Watanabe, K.; Katoh, T. Bioorg. Med. Chem. Lett. 2005, 15, 2583-2585
18. Habel, A.; Boland, W. Org. Biomol. Chem. 2008, 6, 1601-1604
19. Sher, M.; Ali, A.; Reinke, H.; Langer, P. Tetrahedron Lett. 2008, 49, 5400-5402
20. Obushak, M. D.; Matiychuk, V. S.; Turytsya, V. V. Tetrahedron Lett. 2009, 50, 6112-6115
21. Mandal, S. K.; Roy, S. C. Tetrahedron 2008, 64, 11050-11057
22. Pal, S.; Chatare, V.; Pal, M. Curr. Org. Chem. 2011, 15, 782-800
23. Choukchou-Braham, N.; Asakawa, Y.; Lepoittevin, J.-P. Tetrahedron Lett. 1994, 35, 3949-3952
24. Superchi, S.; Minutolo, F.; Pini, D.; Salvadori, P. J. Org. Chem. 1996, 61, 3183-3186
25. Kurosaki, Y.; Fukuda, T.; Iwao, M. Tetrahedron 2005, 61, 3289-3303
26. Uchida, K.; Fukuda, T.; Iwao, M. Tetrahedron 2007, 63, 7178-7186
27. Mandal, S. M.; Roy, S. C. Tetrahedron Lett. 2007, 48, 4131-4134
28. Salvadori, P.; Superchi, S.; Minutolo, F. J. Org. Chem. 1996, 61, 4190-4191
29. Ramacciotti, A.; Fiaschi, R.; Napolitano, E. J. Org. Chem. 1996, 61, 5371-5374
30. Uchida, K.; Watanabe, H.; Kitahara, T. Tetrahedron 1998, 54, 8975-8984
31. Hojo, D.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 5820-5822
32. Rioz-Martínez, A.; de Gonzalo, G.; Torres Pazmiño, D. E.; Fraaije, M. T.; Gotor, V. J. Org. Chem. 2010, 75, 2073-2076
33. Ning, Z.; Jin, R.; Ding, J.; Gao, L. Synlett 2009, 2291-2294
34. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298-3300
35. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664-3665
36. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474-15476
37. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332-7335
38. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174-9177
39. Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306-8308
40. Cai, Y.; Liu, X.; Hui, Y.; Jiang, J.; Wang, W.; Chen, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2010, 49, 6160-6164
41. Jaganathan, A.; Garzan, A.; Whitehead, D. C.; Staples, R. J.; Borhan, B. Angew Chem., Int. Ed. 2011, 50, 2593-2596
42. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Org. Lett. 2011, 13, 2738-2741
43. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164-9167
44. Tan, C. K.; Chen, F.; Yeung, Y.-Y. Tetrahedron Lett. 2011, 52, 4892-4895
45. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335-1339
46. Castellanos, A.; Fletcher, S. P. Chem.-Eur. J. 2011, 17, 5766-5776
47. Cai, Y.; Liu, X.; Jiang, J.; Chen, W.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 5636-5639
48. Chen, Z.-M.; Zhang, Q.-W.; Chen, Z.-H.; Li, H.; Tu, Y.-Q.; Zhang, F.-M.; Tian, J.-M. J. Am. Chem. Soc. 2011, 133, 8818-8821
49. Li, H.; Zhang, F.-M.; Tu, Y.-Q.; Zhang, Q.-W.; Chen, Z.-M.; Chen, Z.-H.; Li, J. Chem. Sci. 2011, 2, 1839-1841
50. Synder, S. A.; Treitler, D. S.; Brucks, A. P. Aldrichimica Acta 2011, 44, 27-40
51. Lozano, O.; Blessley, G.; Martinez del Campo, T.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 8105-8109
52. Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655-20660
53. Song, C. E. Cinchona Alkaloids in Synthesis & Catalysis; Wiley-VCH: Weinheim, Germany, 2009.
54. Li, H.; Chen, Y.; Deng, L. In Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.; Wiley-VCH: Weinheim, Germany, 2011; pp 361-408.
55. Ramana, C. V.; Reddy, C. N.; Gonnade, R. G. Chem. Commun. 2008, 3151-3153
56. Berti, G. J. Org. Chem. 1959, 24, 934-938
57. Yoshikawa, M.; Shimada, H.; Yagi, N.; Murakami, N.; Shimoda, H.; Yamahara, J.; Matsuda, H. Chem. Pharm. Bull. 1996, 44, 1890-1898
58. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1975; Vol. 1, pp 249-264.
59. von Angerer, S.; von Angerer, E.; Ambros, R.; Wiegrebe, W. Arch. Pharm. 1992, 325, 425-431
60. Atta-ur-Rahman, H. E. J. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L); Elsevier Science: Amsterdam, 2006; Vol. 32.
61. Beck, J. J.; Chou, S.-C. J. Nat. Prod. 2007, 70, 891
62. Willis, M. C. Angew. Chem., Int. Ed. 2010, 49, 6026-6027
63. Zhang, B.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2009, 11, 4712-4715
64. Shahzad, S. A.; Vivant, C.; Wirth, T. Org. Lett. 2010, 12, 1364-1367
65. Shahzad, S. A.; Venin, C.; Wirth, T. Eur. J. Org. Chem. 2010, 12, 4110-4113
66. Bendall, V. I.; Dharamshi, S. S. J. Chem. Soc., Perkin Trans. 1 1972, 21, 2732-2734
67. Marco, T.; Gerd, S. Ger. Offen. 1988, 7, 1-8. DE 3644463 A1.
68. Bowden, K.; Ghadir, K. D. F. J. Chem. Soc., Perkin Trans. 2 1990, 8, 1333-1338
69. Izumi, T.; Morishita, N. J. Heterocycl. Chem. 1994, 31, 145-152
70. Mal, D.; Majumdar, G.; Pal, R. J. Chem. Soc., Perkin Trans. 1 1994, 1115-1116
71. Berti, G. Tetrahedron 1958, 4, 393-402