Dicobaltoctacarbonyl-mediated synthesis of tricyclic 5,6-diydropyran-2-one derivatives via tandem cycloaddition reaction between cis-epoxyalkynes, a tethered olefin, and carbon monoxide

Journal of Organic Chemistry

Volumn 72, Issue 2, 2007, Pages 567-573

  Odedra, Arjan ^a   Lush, Shie Fu ^b   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b YUANPEI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CIS-EPOXYALKYNES; COBALT CARBONYL COMPLEX; CYCLOPENTANONE; TANDEM CYCLOADDITION REACTION;

CARBON MONOXIDE; CARBONYLATION; DERIVATIVES; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

2 PYRONE DERIVATIVE; 5,6 DIHYDROPYRAN 2 ONE DERIVATIVE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; COBALT CARBONYL COMPLEX; DICOBALTOCTACARBONYL DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ADDUCTION; ARTICLE; CYCLIZATION; CYCLOADDITION; PAUSON KHAND REACTION; PRODUCT RECOVERY; REACTION ANALYSIS; SYNTHESIS; TANDEM REPEAT;

ALKENES; ALKYNES; CARBON MONOXIDE; COBALT; CYCLIZATION; EPOXY COMPOUNDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PYRANS; STEREOISOMERISM;

EID: 33846221556     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0620617     Document Type: Article

References (77)

1. For general reviews, see: (a) Ho, T.-L. Topics of Organic Synthesis; Wiley-Interscience: New York, 1994; p 79.
2. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
3. (c) Winkler, J. D. Chem. Rev. 1996, 96, 167.
4. (d) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
5. Hegedus, L. S. In Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, CA, 1999.
6. For selected reviews, see: (a) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricaa, D. J. Pure. Appl. Chem. 1992, 64, 1813.
7. (b) Grigg, R. J. Heterocycl. Chem. 1994, 31, 631.
8. (c) de Meijere, A.; Meyer, P. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
9. For selected examples, see: (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701.
10. (b) Overman, L. E. Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1993, 115, 2042.
11. (c) Trost, B. M.; Shen, H. Angew. Chem., Int. Ed. 2001, 40, 2313.
12. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632.
13. (e) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002, 124, 6512.
14. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans. 1 1973, 975.
15. 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.
16. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911.
17. (c) Jeong, N. In Transition Metals in Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, p 560.
18. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
19. (e) Bonaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
20. Harrington, P. J. In Transition Metals in Total Synthesis; Wiley: New York, 1990; p 259.
21. (a) Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
22. (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.
23. (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
24. (d) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-E. Synlett 1991, 204.
25. (e) Shiu, Y.-T.; Madhushaw, R. J.; Li, W.-T.; Lee, G.-H.; Peng, S. H.; Liao, F.-L.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1999, 121, 4066.
26. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc. Perkin Trans. 1 1973, 977.
27. (b) Rautenstrauch, V.; Megard, P.; Conesa, J.; Kuster, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413.
28. (c) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
29. (d) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793.
30. (e) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
31. (f) Jeong, N.; Hwang, S. H.; Lee, Y. K.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
32. (g) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142.
33. (h) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782.
34. (i) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.
35. (j) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
36. (k) Krafft, M. E.; Hirosawa, C.; Bonaga, L. V. R. Tetrahedron Lett. 1999, 40, 9171.
37. Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589.
38. (m) Kim, S.-W.; Son, S. U.; Lee, S. I.; Hyeon, T.; Chung, Y. K. J. Am. Chem. Soc. 2000, 122, 1550.
39. (n) Jiang, B.; Xu, M. Org. Lett. 2002, 4, 4077.
40. (o) Hayashi, M.; Hashimoto, Y.; Yamamoto, Y.; Usuki, J.; Saigo, K. Angew. Chem., Int. Ed. 2000, 39, 631
41. (p) Tang, Y.; Deng, L.; Zhang, Y.; Dong, G.; Chen, J.; Yang, Z. Org. Lett. 2005, 7, 593.
42. For Ti, see: (a) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450.
43. (b) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881.
44. For Ni, see: (c) Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498.
45. For Ru, see: (d) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
46. (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
47. For Rh, see: (f) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
48. (g) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
49. For Ir, see: (h) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852.
50. (a) Van Ornum, S. G.; Cook, J. M. Tetrahedron Lett. 1996, 37, 7185.
51. (b) Van Ornum, S. G.; Cook, J. M. Tetrahedron Lett. 1997, 38, 3657.
52. (c) Son, S. U.; Yoon, Y. A.; Choi, D. S.; Park, J. K.; Kim, B. M.; Chung, Y. K. Org. Lett. 2001, 3, 1065.
53. (d) Thommer, M.; Gerber, P.; Keese, R. Chimia 1991, 45, 23.
54. (e) Vander Walls, A.; Keese, R. J. Chem. Soc., Chem. Commun. 1992, 570.
55. (f) Son, S. U.; Chung, Y. K.; Lee, S.-G. J. Org. Chem. 2000, 65, 6142.
56. Molinaro, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076.
57. Allmendinger, M.; Eberhardt, R.; Luinstra, G.; Rieger, B. J. Am. Chem. Soc. 2002, 124, 5646.
58. (a) Lee, J.-T.; Thomas, P. J.; Alper, H. J. Org. Chem. 2001, 66, 5424.
59. (b) Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174.
60. (c) Drent, E.; Kragtwijk, E. Eur. Pat. Appl. EP 577, 206; Chem. Abstr. 1994, 120, 191517e.
61. For a review, see: Ley, S. V.; Cox, L. R.; Meek, G. Chem. Rev. 1996, 96, 423.
62. (a) Madhushaw, R. J.; Li, C.-L.; Shen, K.-H.; Hu, C.-C.; Liu, R.-S. J. Am. Chem. Soc. 2001, 123, 7427.
63. (b) Madhushaw, R. J.; Lin, M.-Y.; Sohel, S. M. A.; Liu, R.-S. J. Am. Chem. Soc. 2004, 126, 6895.
64. (c) Lin, M.-Y.; Madhushaw, R. J.; Liu, R.-S. J. Org. Chem. 2004, 69, 7700.
65. (d) Maddirala, S. J.; Odedra, A.; Taduri, B. P.; Liu, R.-S. Synlett 2006, 1173.
66. (e) Lo, C.-Y.; Pal, S.; Odedra, A.; Liu, R.-S. Tetrahedron Lett. 2003, 44, 3143.
67. For the early communication of this paper, see: Odedra, A.; Wu, C.-J.; Madhushaw, R. J.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 9610.
68. For metal-stabilized cyclic allene species, see: (a) Yin, J.; Abboud, K. A.; Jones, W. M. J. Am. Chem. Soc. 1993, 115, 3810.
69. (b) Jones, W. M.; Klosin, J. Adv. Organomet. Chem. 1998, 42, 147.
70. The x-ray crystallographic data of compounds 4a, 4b, and 6a have been reported in Supporting Information of the early communication of this work; see ref 16.
71. Krafft, M. E.; Scott, I. L.; Romero, R. H. Tetrahedron Lett. 1992, 33, 3829.
72. For a mechanistic discussion on the effect of the heteroatom on the Pauson-Kand reaction, see: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
73. The m-CPBA-epoxidation shows good diastereoselectivity for cis-allylic alcohol and gave excellent threo-selectivity; see: Rossiter, B. R.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 20, 1979.
74. Wu, C.-Y.; Jan, J.-T.; Ma, S.-H.; Kuo, C.-J.; Juan, H.-F.; Cheng, Y.-S. E.; Hsu, R-H.; Huang, H.-C.; Wu, D.; Brik, A.; Liang, F.-S.; Liu, R.-S.; Fang, J.-M.; Chen, S.-T.; Liang, P.-H.; Wong, C.-H. Proc. Nat. Acad. Sci. 2004, 101, 10012.
75. Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
76. Hayashi, M.; Hashimoto, Y.; Yamamoto, Y.; Usuki, J.; Saigo, K. Angew. Chem., Int. Ed. 2000, 39, 631.
77. Tang, Y.-F.; Deng, L.-J.; Zhang, Y.-D.; Dong, G.-B.; Chen, J.-H.; Yang, Z. Org. Lett. 2005, 7, 593.