General and highly α-regioselective zinc-mediated prenylation of aldehydes and ketones

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1831-1837

  Zhao, Li Ming ^a   Jin, Hai Shan ^a   Wan, Li Jing ^a   Zhang, Li Ming ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVES; GOOD YIELD; PRENYLATION; REGIO-SELECTIVE; REGIOCHEMICAL; REGIOCONTROL;

ALDEHYDES; BROMINE COMPOUNDS; CARBONYLATION; KETONES; REGIOSELECTIVITY; ZINC;

ORGANIC COMPOUNDS;

ALCOHOL DERIVATIVE; ALDEHYDE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; HEMPA; KETONE; SOLVENT; ZINC;

ARTICLE; CHEMICAL REACTION; PRENYLATION; SYNTHESIS; TEMPERATURE;

ALDEHYDES; CATALYSIS; KETONES; PRENYLATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; ZINC;

EID: 79953887253     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102516a     Document Type: Article

References (75)

1. (a) Thomasar, A. F.; Bessiere, Y. In The Total Synthesis of Natural Products; ApSimon, J. W., Ed.; Wiley: New York, 1988; Vol 7, pp 275-454.
2. (b) Mann, J.; Davidson, R. S.; Hobbs, J. B.; Banthorpe, D. V.; Harborne, J. B. In Natural Products: Their Chemistry and Biological Significance; Longman Scientific & Technical: Essex, 1994; pp 289-359.
3. (c) Poyser, J. P.; Hirtzbac, F. D.; Ourisson, G. Tetrahedron 1974, 30, 977-986.
4. (d) Papageorgiou, V. P.; Assimopoulou, A. N.; Couladouros, E. A.; Hepworth, D. H.; Nicolaou, K. C. Angew. Chem., Int. Ed. 1999, 38, 270-300.
5. (e) Papageorgiou, V. P.; Assimopoulou, A. N.; Samanidou, V. F.; Papadoyannis, I. N. Curr. Org. Chem. 2006, 10, 2123-2142.
6. (a) Koepler, O.; Laschat, S.; Baro, A.; Fischer, P.; Miehlich, B.; Hotfilder, M.; le Viseur, C. Eur. J. Org. Chem. 2004, 17, 3611-3622.
7. (b) Roulland, E.; Ermolenko, M. S. Org. Lett. 2005, 7, 2225-2228.
8. (c) Gebauer, J.; Blechert, S. Synlett. 2005, 18, 2826-2828.
9. (d) Eckelbarger, J. D.; Wilmot, J. T.; Epperson, M. T.; Thakur, C. S.; Shum, D.; Antczak, C.; Tarassishin, L.; Djaballah, H.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 4293-4306.
10. (e) Kamata, K.; Hirano, T.; Kuzuya, S.; Mizuno, N. J. Am. Chem. Soc. 2009, 131, 6997-7004.
11. (a) Rodríguez Brasco, M. F.; Genzano, G. N.; Palermo, J. A. Steroids 2007, 72, 908-913.
12. (b) Yoshikawa, M.; Nakamura, S.; Li, X.; Matsuda, H. Chem. Pharm. Bull. 2008, 56, 695-700.
13. (c) Gao, X.; Zhang, Z. X.; Jia, Z. J. Helv. Chim. Acta 2008, 91, 1934-1939.
14. (d) Reddy, P.; Urban, S. Phytochemistry 2009, 70, 250-255.
15. (e) Nakamura, S.; Iwami, J.; Matsuda, H.; Mizuno, S.; Yoshikawa, M. Tetrahedron 2009, 65, 2443-2445.
16. (f) Zhang, P.; Bao, B.; Dang, H. T.; Hong, J.; Lee, H. J.; Yoo, E. S.; Bae, K. S.; Jung, J. H. J. Nat. Prod. 2009, 72, 270-275.
17. (g) Lee, C. L.; Chiang, L. C.; Cheng, L. H.; Liaw, C. C.; Abd El-Razek, M. H.; Chang, F. R.; Wu, Y. C. J. Nat. Prod. 2009, 72, 1568-1572.
18. (a) Nicolaou, K. C.; Hepworth, D. Angew. Chem., Int. Ed. 1998, 37, 839-841.
19. (b) Couladouros, E. A.; Strongilos, A. T.; Papageorgiou, V. P.; Plyta, Z. F. Chem.-Eur. J. 2002, 8, 1795-1803.
20. (c) Cheng, H. S.; Loh, T. P. J. Am. Chem. Soc. 2003, 125, 4990-4991.
21. (d) Tan, K. T.; Chng, S. S.; Cheng, H. S.; Loh, T. P. J. Am. Chem. Soc. 2003, 125, 2958-2963.
22. (e) Tsubuki, M.; Matsuo, S.; Honda, T. Heterocycles 2005, 66, 535-542.
23. (f) Cheng, H. S.; Loh, T. P. Pure Appl. Chem. 2005, 77, 1199-1206.
24. (g) Sagnou, M.; Strongilos, A.; Hadjipavlou-Litina, D.; Couladouros, E. A. Lett. Drug Des. Discovery 2009, 6, 172-177.
25. (h) Nokami, J.; Nomiyama, K.; Matsuda, S.; Imai, N.; Kataoka, K. Angew. Chem., Int. Ed. 2003, 42, 1273-1276.
26. (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763-2794.
27. (b) Loh, T. P.; Zhou, J. R.; Zheng, Y. Org. Lett. 1999, 1, 1855-1857.
28. (c) Moslin, R. M.; Jamison, T. F. J. Org. Chem. 2007, 72, 9736-9745.
29. (d) Ma, C.; Schiltz, S.; Le Goff, X. F. Chem.-Eur. J. 2008, 14, 7314-7323.
30. (e) Zhang, Z.; Huang, J.; Ma, B.; Kishi, Y. Org. Lett. 2008, 10, 3073-3076.
31. (f) Fleury, L. M.; Ashfeld, B. L. Org. Lett. 2009, 11, 5670-5673.
32. (g) Sinha, P.; Roy, S. Chem. Commun. 2001, 1798-1799.
33. (a) Guo, B. S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 4710-4711.
34. (b) Matsukawa, S.; Funabashi, Y.; Imamoto, T. Tetrahedron Lett. 2003, 44, 1007-1010.
35. (c) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
36. (d) Hamann-Gaudinet, B.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1998, 567, 39-47.
37. (e) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 8955-8956.
38. (f) Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130-6141.
39. Estevez, E.; Justicia, J.; Bazdi, B.; Fuentes, N.; Paradas, M.; Choquesillo-Lazarte, D.; Garcia-Ruiz, J. M.; Robles, R.; Gansauer, A.; Cuerva, J. M.; Oltra, J. E. Chem.-Eur. J. 2009, 15, 2774-2791.
40. Zhao, L. M.; Xu, D. F.; Zhou, W.; Li, S. S. Lett. Org. Chem. 2008, 5, 234-236.
41. (a) Terada, A.; Tanoue, Y.; Hatada, A.; Sakamoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 205-213.
42. (b) Braun, M.; Bauer, C. Liebigs Ann. Chem. 1991, 1157-1164.
43. (c) Torii, S.; Akiyama, K.; Yamashita, H.; Inokuchi, T. Bull. Chem. Soc. Jpn. 1995, 68, 2917-2922.
44. Couladouros, E. A.; Plyta, Z. F.; Strongilos, A. T.; Papageorgiou, V. P. Tetrahedron Lett. 1997, 38, 7263-7266.
45. (e) Lu, Q.; Duan, W. H.; Cai, J. C. Chin. Chem. Lett. 2002, 13, 113-114.
46. (f) Yang, H.; Li, Q.; Bao, J. X.; Lu, W.; Aisa, H. A.; Cai, J. C. Chin. Chem. Lett. 2002, 13, 515-518.
47. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
48. (a) Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527-6535.
49. (b) Reich, H. J.; Sikorski, W. H. J. Org. Chem. 1999, 64, 14-15.
50. Reich, H. J.; Borst, J. P.; Dykstra, R. R. Tetrahedron 1994, 50, 5869-5880.
51. (d) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386-13387.
52. (e) Reich, H. J.; Borst, J. P.; Dykstra, R. R.; Green, P. D. J. Am. Chem. Soc. 1993, 115, 8728-8741.
53. (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1-44.
54. Normant, H. Angew. Chem., Int. Ed. 1967, 6, 1046-1067.
55. (a) Ozutsumi, K.; Abe, Y.; Takahashi, R.; Ishiguro, S. J. Phys. Chem. 1994, 98, 9894-9899.
56. Abe, Y.; Ishiguro, S. J. Solution Chem. 1991, 20, 793-803.
57. Abe, Y.; Ozutsumi, K.; Ishiguro, S. J. Chem. Soc., Faraday Trans. 1 1989, 85, 3747-3756.
58. (b) Ishiguro, S.; Ozutsumi, K.; Ohtaki, H. Bull. Chem. Soc. Jpn. 1987, 60, 531-538.
59. (c) Ishiguro, S.; Ozutsumi, K.; Ohtaki, H. J. Chem. Soc., Faraday Trans. 1 1988, 84, 2409-2419.
60. (d) Suzuki, H.; Ishiguro, S.; Ohtaki, H. J. Chem. Soc., Faraday Trans. 1990, 86, 2179-2185.
61. (a) Hoffmann, R. W. Angew. Chem., Int. Ed. 1982, 21, 555-566.
62. (b) Isaac, M. B.; Chan, T.-H. Tetrahedron Lett. 1995, 36, 8957-8960.
63. (c) Kira, M.; Zhang, L. C.; Kabuto, C.; Sakurai, H. Organometallics 1996, 15, 5335-5341.
64. (d) Hada, M.; Nakatsuji, H.; Ushio, J.; Izawa, M.; Yokono, H. Organometallics 1993, 12, 3398-3404.
65. (e) Yamamoto, Y.; Maruyama, K. Heterocycles 1982, 18, 357-386.
66. (f) Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577-2586.
67. Benkeser, R. A.; Broxterman, W. E. J. Am. Chem. Soc. 1969, 91, 5162-5163.
68. (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
69. (b) Jensen, W. B. The Lewis Acid-Base Concepts; Wiley: New York, 1980; Chapter 4, pp 136-137.
70. (c) Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638.
71. (a) Jones, P.; Knochel, P. Chem. Commun. 1998, 2407-2408.
72. (b) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186-195.
73. Birney, D. M.; Xu, X.; Ham, S. Angew. Chem., Int. Ed. 1999, 38, 189-193.
74. Jones, P.; Millot, N.; Knochel, P. Chem. Commun. 1998, 2405-2406.
75. Zinc powder was activated using acetic acid in MeOH. After 20min of stirring, the metal was filtered, washed, and dried under full vacuum for 3 h.