Tandem sequence of cross metathesis-ring-closing metathesis reaction of alkynyl silyloxy-tethered enynes

Journal of the American Chemical Society

Volumn 127, Issue 26, 2005, Pages 9410-9415

  Park, Sangho ^a   Kim, Mansuk ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALKYNES; CROSS METATHESIS; STEREOSELECTIVITY;

SILICON COMPOUNDS;

ALKENE; ALKYNE; SILANE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALKADIENES; ALKENES; ALKYNES; CYCLIZATION; ETHERS; MODELS, CHEMICAL; SILANES; SILOXANES;

EID: 21644464686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0520159     Document Type: Article

References (87)

1. For reviews, see: (a) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317-1382.
2. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1-18.
3. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133-154.
4. (d) Mori, M. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204.
5. First report of enyne RCM: (e) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737-738.
6. For the first enyne metathesis with Grubbs catalyst, see: (f) Kinoshita, A.; Mori, M. Synlett 1994, 1020-1022.
7. For reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. Acc. Chem. Res. 1995, 28, 446-452.
8. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036-2056.
9. (c) Grubbs, R. H.; Chang. S. Tetrahedron 1998, 54, 4413-4449.
10. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
11. (e) Blechert, S. Pure Appl. Chem. 1999, 71, 1393-1399.
12. (f) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89.
13. (g) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
14. (h) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
15. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
16. (j) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim. Germany, 2003, Vol. 2.
17. For diyne metathesis, see: (a) Katz, T. J.; McGinnis, J. J. Am. Chem. Soc. 1975, 97, 1592-1594.
18. (b) Wengrovius, J. H.; Sancho, J. J. Am. Chem. Soc. 1981, 103, 3932-3934.
19. (c) Schrock, R. R.; Clark, D. N.; Sancho, J.; Wengrovius, J. H.; Rocklage, S. M.; Pedersen, S. F. Organometallics 1982, 1, 1645-1651.
20. (d) Fürstner, A.; Seidel, G. Angew. Chem., Int. Ed. 1998, 37, 1734-1736.
21. (e) Fürstner, A.; Mathes, C.; Lehmann, C. W. J. Am. Chem. Soc. 1999, 121, 9453-9454.
22. (f) Fürstner, A.; Guth, O.; Rumbo, A.; Seidel, G. J. Am. Chem. Soc. 1999, 121, 11108-11113.
23. (g) Fürstner, A.; Mathes, C. Org. Lett. 2001, 3, 221-223.
24. (h) Fürstner, A.; Castanet, A.-S.; Radkowski, K.; Lehmann, C. W. J. Org. Chem. 2003, 68, 1521-1528.
25. For a review, see: (a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
26. For a leading reference, see: (b) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370 and references therein.
27. Miller, R. L.; Maifeld, S. V.; Lee, D. Org. Lett. 2004, 6, 2773-2776.
28. For reviews of silicon tethers, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
29. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813-854.
30. (c) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338.
31. For silyloxy-tethered diene RCM reactions, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760.
32. (b) Evans, P. A.; Murthy, S. J. Org. Chem. 1998, 63, 6768-6769.
33. (c) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429-1432.
34. (d) Shu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259.
35. (e) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969.
36. (f) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868.
37. (g) Van de Weghe, P.; Aoun, D.; Boiteau, J.-G.; Eustache, J. Org. Lett. 2002, 4, 4105-4108.
38. (h) Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734-1737.
39. (i) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702-14703.
40. For silyloxy-tethered enyne RCM. see: (a) Semeril, D.; Cleran, M.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2001, 343, 184-198.
41. (b) Yao, Q. Org. Lett. 2001, 3, 2069-2072.
42. (c) Semeril, D.; Cleran, M.; Perez, A. J.; Bruneau, C.; Dixneuf, P. H. J. Mol. Catal. A 2002, 190, 9-25.
43. (a) Antras, F.; Ahmar, M.; Cazes, B. Tetrahedron Lett. 2001, 42, 8157-8160.
44. (b) Trost, B. M.; Machacek, M.; Schnaderbeck, M. J. Org. Lett. 2000, 2, 1761-1764.
45. (c) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076-3079.
46. Hansen, E.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582-9583.
47. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
48. For the inhibition of RCM by a silyl substituent at the terminal position of alkynes. see: (a) Kim, S.-H.; Zeurcher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
49. (b) Clark, S. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973-1982.
50. For resio- and stereoselective cross enyne metathesis with silylated alkynes. see: Kim, M.; Park, S.; Maifeld, S. V.; Lee, D. J. Am. Chem. Soc. 2004, 126, 10242-10243.
51. For a discussion of preferred alkene initiation, see: Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2004, 126, 15074-15080.
52. For related CM-RCM sequences with an alkene and a diyne. see: Stragies, R.; Schuster, M.; Blechert, S. Chem. Commun. 1999, 237-239.
53. An endo-mode ring closure to form a six-membered ring has been observed with substrates that have 1,1-disubstituted alkene moieties: (a) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258-1259.
54. (b) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678-693.
55. (c) Dolhem, F.; Lievre, C.; Demailly, G. Eur. J. Org. Chem. 2003, 2336-2342.
56. Tonogaki, K.; Mori, M. Tetrahedron Lett 2002, 43, 2235-2238.
57. For methods for the formation of alkynylsilyl ethers, see: (a) Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981-6984.
58. (b) Grimm, J. B.; Lee, D. J. Org. Chem. 2004, 69, 8967-8970.
59. For an early mechanistic proposal relying on methylidene as a propagating species, see: Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 56, 2518-2520.
60. Kulkarni, A. A.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 8110-8111.
61. For examples of terminal silylated alkyne metathesis, see. (a) Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235-2238.
62. (b) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465-5468.
63. (c) Lee, H.-Y.; Kim, B. G.; Snapper, M. L. Org. Lett. 2003, 5, 1855-1858.
64. (d) Clark, J. S.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 2629-2630.
65. Full characterization of the CM product was achieved after the conversion of 12 to 12′ via the removal of the silyl moiety; see Supporting Information.
66. Smulik, J. A.; Diver, S. T. Tetrahedron Lett 2001, 42, 171-174.
67. For the mechanistic view in preference of an alkyne initiation- methylidene propagation, see: (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737-738.
68. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020-1022.
69. (c) Stragies, R.; Schuster, M.; Blechert, S. Chem. Commun. 1999, 237-238.
70. For an alkene initiation-alkylidene propagation, see: (d) Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801-10802.
71. For other evidence of an alkene initiation, see: (a) Hoye, T. R.; Donaldson, S. M.; Vos, T. Org. Lett. 1999, 1, 277-280.
72. (b) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274-4277.
73. (c) Giessert, A. J.; Diver, S. T. Org. Lett. 2005, 7, 351-354.
74. For theoretical support for alkene initiation, see: (d) Straub, B. F.; Lippstreu, J. J. J. Am. Chem. Soc. 2005, 127, 7444-7457.
75. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
76. (b) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
77. (c) Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.
78. The metathesis of 34 with ethylene produced 35 in quantitative yield within an hour.
79. For the related ethereal oxygen chelate formation, see: (a) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
80. (b) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
81. (c) Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488-1489.
82. (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.
83. (e) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209-2212.
84. For the formation of a stable alkene chelate, see ref 26b.
85. For early observations of the activating effect of oxygen and nitrogen substituent in enyne metathesis, see: (a) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224-226.
86. (b) Tonogaki, K.; Mori, M. Tetrahedron Lett, 2002, 43, 2235-2238.
87. (c) Randl, S.; Lucas, N.; Connon, S. J.; Blechert, S. Adv. Synth. Catal. 2002, 344, 631-633.