Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst

Organic Letters

Volumn 14, Issue 24, 2012, Pages 6290-6293

  Fang, Chao ^a   Paull, Daniel H ^a   Hethcox, J Caleb ^a   Shugrue, Christopher R ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALKENE; BROMINATED HYDROCARBON; CARBOXYLIC ACID; IODINATED HYDROCARBON; LACTONE; NAPHTHOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ALKENES; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; HYDROCARBONS, BROMINATED; HYDROCARBONS, IODINATED; LACTONES; MOLECULAR STRUCTURE; NAPHTHOLS; STEREOISOMERISM;

EID: 84871589285     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3030555     Document Type: Article

References (43)

1. Chen, G.; Ma, S. Angew. Chem., Int. Ed. 2010, 49, 8306-8308
2. Tan, C. K.; Zhou, L.; Yeung, Y. Synlett 2011, 1335-1339
3. Snyder, S. A.; Treitler, D. S.; Brucks, A. P. Aldrichimica Acta 2011, 44, 27-40
4. Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed. 2012, 51, 10938-10953
5. Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171-197
6. Ranganathan, S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaraman, N. Tetrahedron 2004, 60, 5273-5308
7. Lava, M. S.; Banerjee, A. K.; Cabrera, E. V. Curr. Org. Chem. 2009, 13, 720-730
8. Rodriguez, F.; Fananas, F. J. In Handbook of Cyclization Reactions; Ma, S., Ed.; Wiley-VCH: New York, 2010; Vol. 4, pp 951-990.
9. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664-3665
10. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174-9177
11. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y. J. Am. Chem. Soc. 2010, 132, 15474-15476
12. Tan, C. K.; Zhou, L.; Yeung, Y. Org. Lett. 2011, 13, 2738-2741
13. Tan, C. T.; Le, C.; Yeung, Y. Chem. Commun. 2012, 48, 5793-5795
14. Zhang, W.; Liu, N.; Schienebeck, C. M.; Decloux, K.; Zheng, S.; Werness, J. B.; Tang, W. Chem.-Eur. J. 2012, 18, 7296-7305
15. Murai, K.; Nakamura, A.; Matsushita, T.; Shimura, M.; Fujioka, H. Chem.-Eur. J. 2012, 18, 8448-8453
16. Jiang, X.; Tan, C. K.; Zhou, L.; Yueng, Y. Angew. Chem., Int. Ed. 2012, 51, 7771-7775
17. Paull, D. H.; Fang, C.; Donald, J. R.; Pansick, A. D.; Martin, S. F. J. Am. Chem. Soc. 2012, 134, 11128-11131
18. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298-3300
19. Wang, M.; Gao, L. X.; Mai, W. P.; Xia, A. X.; Wang, F.; Zhang, S. B. J. Org. Chem. 2004, 69, 2874-2876
20. Ning, Z.; Jin, R.; Ding, J.; Gao, L. Synlett 2009, 2291-2294
21. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332-7335
22. Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 6068-6071
23. Tungen, J. E.; Nolsoe, J. M. J.; Hansen, T. V. Org. Lett. 2012, 14, 5884-5887.
24. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330-5334
25. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335-5340
26. Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380
27. Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197-198
28. Ikeuchi, K.; Ido, S.; Yoshimura, S.; Asakawa, T.; Inai, M.; Hamashima, Y.; Kan, T. Org. Lett. 2012, 14, 6016-6019.
29. Seeman, M.; Schöller, M.; Kudis, S.; Helmchen, G. Eur. J. Org. Chem. 2003, 2122-2127
30. Röhrig, S.; Hennig, L.; Findeisen, M.; Welzel, P. Tetrahedron 1998, 54, 3439-3456
31. Canham, S. M.; France, D. J.; Overman, L. E. J. Am. Chem. Soc. 2010, 132, 7876-7877
32. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-CVH: New York, 2000; pp 231-280.
33. Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, 1 st ed.; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; Vol. 2, pp 649-677.
34. Katsuki, T. Adv. Synth. Catal. 2002, 344, 131-147
35. Shi, Y. Acc. Chem. Res. 2004, 37, 488-496
36. Yang, D. Acc. Chem. Res. 2004, 37, 497-505
37. Denmark, S. E.; Wu, Z. Synlett 1999, 847-859
38. Shibasaki, M.; Kanai, M.; Matsunaga, S. Aldrichachim. Acta 2006, 39, 31-39
39. Zhang, F.-Y.; Corey, E. J. Org. Lett. 1999, 1, 1287-1290
40. Page, P. C. B.; Buckley, N. R.; Blacker, A. J. Org. Lett. 2004, 6, 1543-1546
41. Marigo, M.; Franzen, J.; Poulsen, T. B.; Zhuang, W.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964-6965
42. Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413-11424
43. Recently Shi reported a modified fructose-derived ketone to promote enantioselective epoxidation of limited scope of cis -olefins with good enantioselectivity: Burke, C. P.; Shi, Y. Org. Lett. 2009, 11, 5150-5153