Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 7849-7857

  Allen, Anna ^a   Le Marquand, Paul ^a   Burton, Ryan ^a   Villeneuve, Karine ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DIMERIZATION; ENANTIOSELECTIVITY; LIGANDS; RHODIUM; SALTS; SOLVENTS;

AZABENZONORBORNADIENE; OXABICYCLIC ALKENES; PHOSPHINE;

OLEFINS;

ALKENE DERIVATIVE; BICYCLO COMPOUND; CATION; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; NAPHTHYL GROUP; NORBORNANE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM; SILVER DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; CYCLODIMERIZATION; DIMERIZATION; ENANTIOSELECTIVITY; ISOMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; TEMPERATURE SENSITIVITY;

EID: 35348877890     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7012884     Document Type: Article

References (73)

1. For selected examples, see: (a) Lautens, M.; Fagnou, K.; Heibert, S. Acc. Chem. Res. 2003, 36, 48.
2. (b) Lautens, M.; Hieben, S.; Renaud, J.-L. J. Am. Chem. Soc. 2001, 123, 6834.
3. (c) Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437.
4. (d) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884.
5. (e) Wu, M.-S.; Jeganmohan, M.; Cheng, C.-H. J. Org. Chem. 2005, 70, 9545.
6. (f) Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373.
7. (g) Zhang, W.; Wang, L.-X.; Shi, W.-J.; Zhou, Q.-L. J. Org. Chem. 2005, 70, 3734.
8. (h) Cabrera, S.; Arrayás, R. G.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. Chem. 2005, 127, 17938.
9. (i) Li, M.; Yan, X.-X.; Zhu, X.-Z.; Cao, B.-X.; Sun, J.; Hou, X.-L. Org. Lett. 2004, 6, 2833 and references therein.
10. For selected examples of molecular architecture, see: (a) Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119.
11. (b) Warrener, R. N.; Margetic, D.; Sun, G.; Amarasekara, A. S.; Foley, P.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1999, 40, 4111.
12. (c) Warrener, R. N.; Butler, D. N.; Margetic, D.; Pfeffer, F. M.; Russell, R. A. Tetrahedron Lett. 2000, 41, 4671.
13. (d) Warrener, R. N. Eur. J. Org. Chem. 2000, 3363.
14. (e) Warrener, R. N.; Margetic, D.; Foley, P.; Butler, D. N.; Winling, A.; Beales, K. A.; Russell, R. A. Tetrahedron 2001, 57, 571.
15. (f) Dalphond, J.; Bazzi, H. S.; Kahrim, K.; Sleiman, H. F. Macromol. Chem. Phys. 2002, 203, 1988.
16. (g) Lautens, M.; Colucci, J. T.; Hieben, S.; Smith, N. D.; Bouchain, G. Org. Lett. 2002, 4, 1879.
17. For our recent studies of Ru-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and alkynes, see: (a) Jordan, R. W.; Tam, W. Org. Lett. 2000, 2, 3031.
18. (b) Jordan, R. W.; Tam, W. Org. Lett. 2001, 3, 2367.
19. (c) Jordan, R. W.; Tam, W. Tetrahedron Lett. 2002, 43, 6051.
20. (d) Villeneuve, K.; Jordan, R. W.; Tam, W. Synlett 2003, 2123.
21. (e) Villeneuve, K.; Tam, K. Angew. Chem., Int. Ed. 2004, 43, 610.
22. (f) Villeneuve, K.; Riddell, N. G.; Jordan, R. W.; Tsui, G.; Tam, W. Org. Lett. 2004, 6, 4543.
23. (g) Jordan, R. W.; Khoury, P. R.; Goddard, J. D.; Tam, W. J. Org. Chem. 2004, 69, 8467.
24. (h) Riddell, N. G.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
25. (i) Riddell, N. G.; Tam, W. J. Org. Chem. 2006, 71, 1943.
26. (j) Liu, P.; Jordan, R. W.; Goddard, J. D.; Tam, W. J. Org. Chem. 2006, 71, 3793.
27. (k) Jordan, R. W.; Villeneuve, K.; Tam, W. J. Org. Chem. 2006, 71, 5830.
28. Villeneuve, K.; Tam, W. Eur. J. Org. Chem. 2006, 5499.
29. Villeneuve, K.; Tam, W. Organometallics 2006, 25, 843.
30. Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514.
31. (a) This reaction was discovered by the Ph.D. student Karine Villeneuve on May 9, 2006, and the results were presented in her Ph.D. thesis which was successfully defended on October 20, 2006: Villeneuve, K. Ph.D. thesis, University of Guelph, 2006.
32. (b) During the preparation of this manuscript, a paper closely related to this study (using a slightly different catalyst precursor) appeared: Nishimura, T.; Kawamoto, T.; Sasaki, K.; Tsurumaki, E.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 1492.
33. GOESY: Gradient enhanced nuclear Overhauser enhancement spectroscopy. See: (a) Stonehouse, J.; Adell, P.; Keeler, J.; Shaka, A. J. J. Am. Chem. Soc. 1994, 116, 6037.
34. (b) Stott, K.; Stonehouse, J.; Keeler, J.; Hwang, T.-L.; Shaka, A. J. J. Am. Chem. Soc. 1995, 117, 4199.
35. (c) Dixon, A. M.; Widmalm, G.; Bull, T. E. J. Magn. Reson. 2000, 147, 266.
36. Lough, A. J.; Allen, A.; Tam, W. Acta Crystallogr. 2007, E63, o1462-o1463.
37. For examples of natural products containing a naphtho[1,2-b]furan ring system, see: (a) Otani, T.; Sugimoto, Y.; Aoyagi, Y.; Igarashi, Y.; Furumai, T.; Saito, N.; Yamada, Y.; Asao, T.; Oki, T. J. Antibiot. 2000, 53, 337.
38. (b) Corey, E. J. J. Am. Chem. Soc. 1955, 77, 1044.
39. (c) Marco, J. A.; Sanz, J. F.; Falco, E.; Jakupovic, J.; Lex, J. Tetrahedron 1990, 46, 7941.
40. (d) Hoeksama, H.; Kruger, W. C. J. Antibiot. 1976, 29, 704.
41. (e) Uchiyama, N.; Kiuchi, F.; Ito, M.; Honda, G.; Takeda, Y.; Khodzhimatov, O. K.; Ashurmetov, O. A. J. Nat. Prod. 2003, 66, 128.
42. (f) Tomoda, H.; Tabata, N.; Masuma, R.; Si, S.-Y.; Omura, S. J. Antibiot. 1998, 51, 618.
43. (g) Butler, M. S.; Capon, R. J. Aust. J. Chem. 1993, 46, 1363.
44. (h) Thomas, R. Pure Appl. Chem. 1973, 34, 515.
45. (i) da Costa, G. M.; de Lemos, T. L. G.; Pessoa, O. D. L.; Monte, F. J. Q.; Braz-filho, R. J. Nat. Prod. 1999, 62, 1044.
46. (j) Gaspar-Marques, C.; Simoes, M. F.; Rodriguez, B. J. Nat. Prod. 2005, 68, 1408.
47. (a) Clive, D. L. J.; Fletcher, S. P. Chem. Commun. 2003, 2464.
48. (b) Kawamata, T.; Nagashima, K.; Nakai, R.; Tsuji, T. Synth. Commun. 1996, 26, 139.
49. (c) Kraus, G. A.; Chen, L. Synlett 1991, 89.
50. (d) Emrich, D. E.; Larock, R. C. J. Organomet. Chem. 2004, 689, 3756.
51. (e) Marino, J. P.; Laborde, E.; Paley, R. S. J. Am. Chem. Soc. 1988, 110, 966.
52. (f) Maertens, F.; Toppet, S.; Compernolle, F.; Hoornaert, G. J. Eur. J. Org. Chem. 2004, 2707.
53. (g) Clive, D. L. J.; Fletcher, S. P.; Liu, D. J. Org. Chem. 2004, 69, 3282.
54. (h) Brimble, M. A.; Elliott, R. J.; Turner, P. Tetrahedron 1998, 54, 14053.
55. (i) Takeya, T.; Doi, H.; Ogata, T.; Okamoto, I.; Kotani, E. Tetrahedron 2004, 60, 9049.
56. (j) Noland, W. E.; Kedrowski, B. L. J. Org. Chem. 1999, 64, 596.
57. For examples of the creation of fused ring systems through dimerization reactions, see: (a) Venkatesh, C.; Ila, H.; Junjappa, H.; Mathur, S.; Huch, V. J. Org. Chem. 2002, 67, 9477.
58. (b) Wu, A.; Chakraborty, A.; Will, D.; Lagona, J.; Damkaci, F.; Ofori, M. A.; Chiles, J. K.; Fettinger, J. C.; Isaacs, L. J. Org. Chem. 2002, 67, 5817.
59. (c) Ohkita, M.; Sano, K.; Suzuki, T.; Tsuji, T. Tetrahedron Lett. 2001, 42, 7295.
60. (d) Abakumov, G. A.; Druzhkov, N. O.; Kurskii, Y. A.; Abakumova, L. G.; Shavyrim, A. S.; Fukin, G. K.; Poddel'skii, A. I.; Cherkasov, V. K.; Okhlopkova, L. S. Russ. Chem. Bull., Int. Ed. 2005, 54, 2571.
61. (e) Klys, A.; Czardybon, W.; Warkentin, J.; Werstuik, N. H. Can. J. Chem. 2004, 82, 1769.
62. (f) Abdou, W. M.; Kamel, A. A. Tetrahedron 2000, 56, 7573.
63. Abbreviations for various phosphine ligands used: dppf, 1,1′-bis-(diphenylphosphino)ferrocene; dppe, 1,2-bis(diphenylphosphino) ethane; (R)- BINAP, (R)-(+)-2,2′-bis(diphenylphosphino)-1, 1′-binaphthyl; (R)-Tol-BINAP, (R)-(+)-2,2′-bis(di-p- tolylphosphino)-1,1′-binaphthyl; (R)-3,5-xylyl-BINAP, (R)-(+)-2,2′-bis(di(3,5-xylyl)phosphino)-1,1′-binaphfhyl; (R,R)-Me- Duphos, (-)-1,2-bis((2R,5R)-2,5- dimethylphospholano)benzene; (S,S)- Chiraphos: (2S,3S)-(-)- bis(diphenylphosphino)butane; (R)-Prophos, (R)- (+)-1,2-bis(diphenylphosphino)propane; (R,S)-Josiphos, (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl] ethyldicyclohexylphosphine ethanol adduct; (S,S)-DIOP, (4S,5S)-(+)-4,5-bis(diphenylphosphinomethyl)-2, 2′-dimethyl-1,3-dioxolane; (S,S)-Norphos, (2S,3S)-(+) -2,3-bis(diphenylphosphino)-bicyclo[2.2.1]hept-5-ene; (S)-phanephos, (S)-(+)-4,12-bis(diphenylphosphino)-[2.2]paracyclophane; (R,R)-Me-BPE, (+)-1,2-bis((2R,5R)-2,5-dimethylphospholano) ethane; (R)-Trost ligand: (1R,2R)-(+)-1,2- diaminocyclohexane-N,N′-bis(2′-diphenylphosphinobenzoyl).
64. For preparations of oxabenzonorbornadienes, see: (a) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
65. (b) Friedman, L.; Logullo, F. M. J. Org. Chem. 1969, 34, 3089.
66. (c) Jung, K. Y.; Masato, K. J. Org. Chem. 1989, 54, 5667.
67. (d) Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884.
68. (e) Lai, Y.-H.; Yong, Y.-L.; Wong, S.-Y. J. Org. Chem. 1997, 62, 4500.
69. (f) Caster, K. C.; Keck, C. G.; Walls, R. D. J. Org. Chem. 2001, 66, 2932.
70. (g) Gribble, G. W.; LeHoullier, C. S.; Sibi, M. P.; Allen, R. W. J. Org. Chem. 1985, 50, 1611.
71. (h) Hart, H.; Bashir-Hashemi, B.; Luo, J.; Meador, M. A. Tetrahedron 1986, 42, 1641.
72. For preparations of azabenzonorbornadienes, see: (a) Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3645.
73. (b) Cho, Y.-H.; Zunic, V.; Senboku, H.; Olsen, M.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 6837.