Tetramethyl thiourea/Co2(CO)8-catalyzed Pauson-Khand reaction under balloon pressure of CO

Organic Letters

Volumn 7, Issue 4, 2005, Pages 593-595

  Tang, Yefeng ^a,b   Deng, Lujiang ^a,b   Zhang, Yandong ^a,b   Dong, Guangbin ^a,b   Chen, Jiahua ^a,b   Yang, Zhen ^a,b,c  

^a PEKING UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c VivoQuest Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBON MONOXIDE; CYCLOPENTENONE DERIVATIVE; TETRAMETHYLTHIOUREA; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; DRUG DERIVATIVE; THIOUREA;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; PAUSON KHAND REACTION; PRESSURE; CHEMISTRY;

CARBON MONOXIDE; CATALYSIS; CYCLIZATION; PRESSURE; THIOUREA;

EID: 14844358604     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047651a     Document Type: Article

References (48)

1. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans. 1 1973, 975.
2. Recent reviews of the Pauson-Khand reaction: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH; Weinheim, Germany, 1998; Vol. 1, p 560. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (e) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
3. Recent reviews of the Pauson-Khand reaction: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH; Weinheim, Germany, 1998; Vol. 1, p 560. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (e) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
4. Recent reviews of the Pauson-Khand reaction: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH; Weinheim, Germany, 1998; Vol. 1, p 560. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (e) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
5. Recent reviews of the Pauson-Khand reaction: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH; Weinheim, Germany, 1998; Vol. 1, p 560. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (e) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
6. Recent reviews of the Pauson-Khand reaction: (a) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 703. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911. (c) Jeong, N. In Transition Metals In Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH; Weinheim, Germany, 1998; Vol. 1, p 560. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263. (e) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
7. (a) Harrington, P. J. In Transition Metals in Total Synthesis; Wiley: New York, 1990; p 259.
8. (a) Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
9. (b) Smit, W. A.; Gybin, A. S.; Shashkov, A. S.; Struchkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Caple, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241.
10. (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
11. (d) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-E. Synlett 1991, 204.
12. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
13. (b) Rautenstrauch, V.; Mégard, P.; Conesa, J.; Küster, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413.
14. (c) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
15. (d) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793.
16. (e) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
17. (f) Jeong, N.; Hwang, S. H.; Lee, Y. K.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
18. (g) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142.
19. (h) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782.
20. (i) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.
21. (j) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
22. (k) Krafft, M. E.; Hirosawa, C.; Bonaga, L. V. R. Tetrahedron Lett. 1999, 40, 9171.
23. (l) Sugihara, T.; Yamaguchi. M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589.
24. (m) Kim, S.-W.; Son, S. U.; Lee, S. I.; Hyeon, T.; Chung, Y. K. J. Am. Chem. Soc. 2000, 122, 1550.
25. (n) Jiang B.; Xu, M. Org. Lett. 2002, 4, 4077.
26. (a) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem Soc. 1996, 118, 9450.
27. (b) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881.
28. Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498.
29. (a) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
30. (b) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
31. (a) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
32. (b) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
33. Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852.
34. (a) Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968.
35. (b) Krafft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693.
36. (c) Krafft, M. E.; Juliano, C. A. J. Org. Chem. 1992, 57, 5106.
37. (d) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
38. (e) Fonquenra, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225.
39. (f) Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 771.
40. (g) Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 1999, 121, 7411.
41. (h) Hayashi, M.; Hashimoto, Y.; Yamamoto, Y.; Usuki, J.; Saigo, K. Angew. Chem., Int. Ed. 2000, 39, 631.
42. (i) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. J. Am. Chem. Soc. 2000, 122, 10242.
43. (a) Yang, N.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297.
44. (b) Miao, H.; Yang, Z. Org. Lett. 2000, 2, 1765.
45. Dai, M.; Wang, C.; Dong, G.; Xiang, J.; Luo, Y.; Liang, B.; Chen, J.; Yang, Z. Eur. J. Org. Chem. 2003, 4346.
46. Dai M.; Liang, B.; Wang, C.; You, Z.; Xiang, J.;Dong, G.; Chen, J.; Yang, Z. Adv. Synth. Catal. 2004, 346, 1669.
47. 8 (8.5 mg, 0.025 mmol), and TMTU (198 mg, 0.15 mmol) in dry benzene (10 mL) was vigorously stirred at 70°C under CO (supplied from a balloon) until the substrate was consumed. The reaction mixture was stirred at same temperature for 1 h. The resulting solution was passed through a small pad of silica gel using a mixed eluent of hexane and ethyl acetate (4/1, v/v). Purification of the crude products by flash chromatography on silica gel afforded pure bicyclic enone 2 (114 mg; 96%).
48. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026.