Ruthenium-catalyzed cycloisomerizations of diynols

Journal of the American Chemical Society

Volumn 127, Issue 13, 2005, Pages 4763-4776

  Trost, Barry M ^a   Rudd, Michael T ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; ISOMERIZATION; ISOMERS; ORGANIC ACIDS; RUTHENIUM; SYNTHESIS (CHEMICAL);

CYCLOISOMERIZATIONS; DIENONES; DIYNOLS;

ALCOHOLS;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; DIENAL DERIVATIVE; DIENONE DERIVATIVE; DIYNOL DERIVATIVE; KAINIC ACID; KETONE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; GEOMETRY; ISOMERIZATION; METHODOLOGY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ALDEHYDES; ALKYNES; CATALYSIS; CYCLIZATION; CYCLOPARAFFINS; ISOMERISM; KETONES; PROPANOLS; RUTHENIUM;

EID: 16844384363     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043097o     Document Type: Article

References (98)

1. Wender, P. A.; Miller, B. L. Org. Synth.: Theory Appl. 1993, 2, 27.
2. Bertz, S. H.; Sommer, T. J. Org. Synth.: Theory Appl. 1993, 2, 67.
3. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
4. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
5. Trost, B. M. Science 1991, 254, 1471.
6. Wolinsky, J.; Gibson, T.; Slabaugh, M. R. J. Org. Chem. 1964, 29, 3740.
7. Wolinsky, J.; Barker, W. J. Am. Chem. Soc. 1960, 82, 636-638.
8. Heathcock, C. H. In Comprehensive organic synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; p 133.
9. Nielsen, A. T.; Houlihan, W. J. Org. React. 1968, 16, 1.
10. House, H. O. Modern synthetic reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; p 629.
11. Carey, F. A.; Sunberg, R. J. Advanced organic chemistry, Part B, 3rd ed.; Plenum Press: New York, 1990.
12. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862-8863.
13. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178-4179.
14. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 1467-1470.
15. Trost, B. M.; Rudd, M. T.; Costa, M. G.; Lee, P. I.; Pomerantz, A. E. Org. Lett. 2004, 5, 4235.
16. Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1083-1084.
17. Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1079-1082.
18. Gensler, W. J.; Abrahams, C. B. J. Am. Chem. Soc. 1958, 80, 4593-4596.
19. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394.
20. Fried, J.; Lin, C. H.; Dalven, P.; Sih, J. C. J. Am. Chem. Soc. 1972, 94, 4343.
21. Fried, J.; Lin, C. H.; Ford, S. H. Tetrahedron Lett. 1969, 1379.
22. Turner, J. J.; Leeuwenburgh, M. A.; Van Der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 2001, 42, 8713-8716.
23. Gronquist, M. R.; Meinwald, J. J. Org. Chem. 2001, 66, 1075-1081.
24. Ding, C. H.; Dai, L. X.; Hou, X. L. Synlett 2004, 1691-1694.
25. Yamaguchi, M.; Nobayashi, Y.; Hirao, I. Tetrahedron 1984, 40, 4261-4266.
26. Tsunoda, T.; Nagino, C.; Oguri, M.; Ito, S. Tetrahedron Lett. 1996, 37, 2459-2462.
27. Mitsunobu, O. Synthesis 1981, 1-28.
28. Brown, C. A.; Yamashita, A. J. Am. Chem. Soc. 1975, 97, 891-892.
29. Midland, M. M.; Halterman, R. L.; Brown, C. A.; Yamaichi, A. Tetrahedron Lett. 1981, 22, 4171-4172.
30. Takano, S.; Sekiguchi, Y.; Sato, N.; Ogasawara, K. Synthesis 1987, 139-141.
31. Takano, S.; Shimazaki, Y.; Iwabuchi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619-3622.
32. Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974-9983.
33. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
34. Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1979, 44, 4997-4998.
35. Brown, D. G.; Velthuisen, E. J.; Commerford, J. R.; Brisbois, R. G.; Hoye, T. R. J. Org. Chem. 1996, 61, 2540-2541.
36. Muller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
37. Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Chem. Commun. 1973, 151-152.
38. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 107-108.
39. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
40. Trost, B. M.; Surivet, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15592.
41. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025-5036.
42. Trost, B. M.; Pinkerton, A. B.; Toste, F. D.; Sperrle, M. J. Am. Chem. Soc. 2001, 123, 12504-12509.
43. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
44. Trost, B. M.; Surivet, J. P.; Toste, F. D. J. Am. Chem. Soc. 2001, 123, 2897.
45. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 6138-6138.
46. Trost, B. M.; Brown, R. E.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 5877-5878.
47. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
48. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728-9729.
49. Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739-7743.
50. Yamamoto, Y.; Ishii, J. I.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712-3713.
51. Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143-12160.
52. Yamamoto, Y.; Hata, K.; Arakawa, T.; Itoh, K. Chem. Commun. 2003, 1290-1291.
53. Varela, J. A.; Castedo, L.; Saa, C. Org. Lett. 2003, 5, 2841-2844.
54. Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610-9611.
55. Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310-4319.
56. Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2001, 1102-1103.
57. Yamamoto, Y.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6189-6190.
58. Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119.
59. Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28-29.
60. Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 6844-6845.
61. Le Paih, J.; Monnier, F.; Derien, S.; Dixneuf, P. H.; Clot, E.; Eisenstein, O. J. Am. Chem. Soc. 2003, 125, 11964-11975.
62. Le Paih, J.; Derien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2001, 40, 2912-2915.
63. Le Paih, J.; Derien, S.; Dixneuf, P. H. Chem. Commun. 1999, 1437-1438.
64. Dixneuf, P. H.; Bruneau, C.; Derien, S. Pure Appl. Chem. 1998, 70, 1065-1070.
65. Yoshida, M.; Sugimoto, K.; Ihara, M. Arkivoc 2003, 35-44.
66. Kluge, A. F.; Lillya, C. P. J. Org. Chem. 1971, 36, 1977.
67. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717-6725.
68. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
69. 2.
70. 2 in DME.
71. Fleming, I.; Winter, S. B. D. J. Chem. Soc., Perkin Trans. 1 1998, 2687.
72. Fleming, I.; Roberts, R. S.; Smith, S. C. J. Chem. Soc., Perkin Trans. 1 1998, 1209.
73. See Supporting Information for preparation.
74. Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986, 51, 2655-2661.
75. Crabtree, R. H.; Davis, M. W. Organometallics 1983, 2, 681-682.
76. Brown, J. M.; Hall, S. A. Tetrahedron Lett. 1984, 25, 1393-1396.
77. Evans, D. A.; Morrissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866-3868.
78. Evans, D. A.; Morrissey, M. M. Tetrahedron Lett. 1984, 25, 4637-4640.
79. Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072-1073.
80. Van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195-200.
81. Ager, D. J. Synthesis 1984, 384-398.
82. Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044-6046.
83. Tamao, K.; Kumada, M.; Maeda, K. Tetrahedron Lett. 1984, 25, 321.
84. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
85. Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
86. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207.
87. Yoo, S. E.; Lee, S. H. J. Org. Chem. 1994, 59, 6968-6972.
88. Becker, E.; Mereiter, K.; Puchberger, M.; Schmid, R.; Kirchner, K. Organometallics 2003, 22, 2124-2133.
89. Pavlik, S.; Gemel, C.; Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Org. Chem. 2001, 617, 301-310.
90. Becker, E.; Ruba, E.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 2001, 20, 3851-3853.
91. Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712-2713.
92. Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609-7610.
93. Gemel, C.; Lapensee, A.; Mauthner, K.; Mereiter, K.; Schmid, R.; Kirchner, K. Montash. Chem. 1997, 128, 1189-1199.
94. Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235-8238.
95. Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218-5219.
96. Albers, M. O.; Dewaal, D. J. A.; Lues, D. C.; Robinson, D. J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986, 1680-1682.
97. 75% isotopic purity as measured by mass spectrometric analysis carried out by Dr. David Walthall in the Brauman group at Stanford University on Oct 31, 2001.
98. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2003, 125, 11516.