Ring closing enyne metathesis: Control over mode selectivity and stereoselectivity

Journal of the American Chemical Society

Volumn 126, Issue 46, 2004, Pages 15074-15080

  Hansen, Eric C ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; ETHYLENE; REACTION KINETICS;

MODE SELECTIVITY; RING CLOSING ENYNE METATHESIS; RING CLOSURE REACTIONS;

STEREOCHEMISTRY;

ALKENE; ALKYNE; CYCLOHEXANE DERIVATIVE; ETHYLENE; MACROCYCLIC COMPOUND; RUTHENIUM; TARTARIC ACID DERIVATIVE;

ARTICLE; CONFORMATION; CYCLIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY;

ALKYNES; CYCLIZATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9344256087     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045422d     Document Type: Article

References (88)

1. For reviews on olefin metathesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
2. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. I 1998, 371-388.
3. (c) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399.
4. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043.
5. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
6. (f) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
7. (g) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2.
8. For reviews on enyne metathesis, see: (a) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2, 176-204.
9. (b) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 1317-1382.
10. (c) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1-18.
11. (d) Mori, M. Top. Organomet. Chem. 1998, 1, 133-154.
12. For the first example of enyne metathesis, see: (e) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737-738.
13. For the first enyne metathesis with Grubbs catalyst, see: (f) Kinoshita, A.; Mori, M. Synlett 1994, 1020-1022.
14. (a) Katz, T. J.; McGinnis, J. J. Am. Chem. Soc. 1975, 97, 1592-1594.
15. (b) Wengrovius, J. H.; Sancho, J. J. Am. Chem. Soc. 1981, 103, 3932-3934.
16. (c) Schrock, R. R.; Clark, D. N.; Sancho, J.; Wengrovius, J. H.; Rocklage, S. M.; Pedersen, S. F. Organometallics 1982, 1, 1645-1651.
17. (d) Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734-1736.
18. (e) Fürstner, A.; Guth, O.; Rumbo, A.; Seidel, G. J. Am. Chem. Soc. 1999, 121, 11108-11113.
19. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
20. (b) Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801-10802.
21. (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
22. (d) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
23. (e) Huang, J.; Stevens, E. D.; Nolan, S. P.; Peterson, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
24. Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083.
25. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705 and references therein.
26. (a) Kim, S.-H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
27. (b) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298.
28. (c) Codesido, E. M.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 1483-1486.
29. (d) Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2001, 5, 1139-1142.
30. (e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649.
31. (f) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231-8233.
32. (g) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2002, 43, 7469-7472.
33. (h) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417-2420.
34. (i) Wu, C.-J.; Madhushaw, R. J.; Liu, R.-S. J. Org. Chem. 2003, 68, 7889-7892.
35. (j) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047-8049.
36. (k) Honda, T.; Namiki, H.; Kaneda, K.; Mizutani, H. Org. Lett. 2004, 6, 87-89.
37. (l) Boyer, F.-D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817-1820.
38. (m) van Otterlo, W. A. L.; Ngidi, E. L.; de Koning C. B.; Fernandes, M. A. Tetrahedron Lett. 2004, 45, 659-662.
39. (a) Rodriguez, J. R.; Castedo, L.; Mascarenas, J. L. Chem.-Eur. J. 2002, 8, 2923-2930.
40. (b) Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878.
41. (c) Garcia-Fandino, R.; Codesido, E. M.; Sobarzo-Sanchez, E.; Castedo, L.; Granja, J. R. Org. Lett. 2004, 6, 193-196.
42. (d) Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397-4399.
43. (e) Brenneman, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329-1331.
44. (f) Aggarwal, V. K.; Astle, C. J.; Rogers-Evans, M. Org. Lett. 2004, 6, 1469-1471.
45. Mori, M.; Kitamura, T.; Sato, Y. Synthesis 2001, 4, 654-664.
46. For macrocyclic RCEYM, see: (a) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773-775.
47. (b) Morales, C. A.; Layton, M. E.; Shair, M. D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12036-12041.
48. (c) Barrett, A. G. M.; Hennessy, A. J.; Vezouet, R. L.; Procopiou, P. A.; Seale, P. W.; Stefaniak, S.; Upton, R. J.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2004, 69, 1028-1037.
49. Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2518-2520.
50. Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388-12389.
51. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. Tetrahedron 1999, 8155-8176.
52. (c) Smulik, J. A.; Diver, S. T. J. Org. Chem. 2000, 65, 1788-1792.
53. (d) Smulik, J. A.; Giessert, A. J.; Diver, S. T. Tetrahedron Lett. 2002, 43, 209-211.
54. (e) Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235-2238.
55. (f) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org Chem. 2002, 67, 224-226.
56. All previously reported examples required an ethylene atmosphere and therefore do not reflect the inherent selectivity of the RCEYM reaction. See ref 10.
57. Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582-9583.
58. Lee, D.; Sello, J. K.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 10648-10649.
59. (a) Berens, U.; Leckel, D.; Oepen, S. C. J. Org. Chem. 1995, 60, 8204-8208.
60. (b) Dixon, D. J.; Foster, A. C.; Ley, S. V.; Reynolds, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 1635-1638.
61. (c) Ley, S. V.; Michel, P. Synlett 2001, 11, 1793-1795.
62. For a review of the use of 2,3-butanedione diacetal protecting groups, see: (d) Ley, S. V.; Baeschlin, D. K.; Dixon, D. J.; Foster, A. C.; Ince, S. J.; Priepke, H. W. M.; Reynolds, D. J. Chem. Rev. 2001, 101, 53-80.
63. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Org. Lett. 2002, 4, 2035-2038.
64. (a) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161-1163.
65. (b) Rückert, A.; Eisele, D.; Blechert, S. Tetrahedron Lett. 2001, 42, 5245-5247.
66. (c) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803-805.
67. (d) Banti, D.; North, M. Adv. Synth. Catal. 2002, 344, 694-704.
68. Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678-693.
69. Although a noncarbenic mechanism for the formation of cyclopropanes cannot be excluded, we prefer the carbene mechanism because the amount of product formed was proportional to the amount of catalyst used. Peppers, B. P.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 9524-9525.
70. Lee, C. H.; Grubbs, R. H. Org. Lett. 2000, 2, 2145-2147.
71. Lee, H.-Y.; Kim, B. G.; Snapper, M. L. Org. Lett. 2003, 5, 1855-1858.
72. For examples of using 1,3-dienes in RCM, see: (a) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908.
73. (b) Basu, K.; Eppich, J. C.; Paquette, L. A. Adv. Synth. Catal. 2002, 344, 615-618.
74. (c) Randl, S.; Lucas, N.; Connon, S. J.; Blechert, S. Adv. Synth. Catal. 2002, 344, 631-633.
75. (d) Wang, X.; Porco, J. A. J. Am. Chem. Soc. 2003, 125, 6040-6041.
76. Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 3117-3125.
77. An endo-mode ring closure to form a six-membered ring has been observed with substrates that have 1,1-disubstituted alkene moieties; see: (a) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258-1259.
78. (b) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678-693.
79. (c) Dolhem, F.; Lievre, C.: Demailly, G. Eur. J. Org. Chem. 2003, 2336-2342.
80. Some studies indicate that the alkene reacts first in the presence of alkyne with Grubbs catalyst, although the alkynes in these studies are not terminal nor normal internal alkynes, see: (a) Hoye, T. R.; Donaldson, S. M.; Vos, T. Org. Lett. 1999, 1, 277-280.
81. (b) Schramm M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274-4277.
82. For the related complex formation with styrene derivatives, see: (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
83. (b) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
84. (c) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488-1489.
85. (d) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351.
86. 31P NMR δ 50.76). This distinctive behavior is probably due to the steric interaction between the dihydrofuryl group and one of the mesityl groups on the N-heterocyclic carbene ligand of the newly formed complex.
87. Hansen, E. C.; Lee, D. Org. Lett. 2004, 6, 2035-2038.
88. For related reactions, see: Stragies, R.; Schuster, M.; Blechert, S. Chem. Commun. 1999, 237-239.