Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1794-1805

  Chuang, Tsung Hsun ^a   Fang, Jim Min ^a   Jiaang, Weir Torn ^a   Tsai, Yeun Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001211298     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951980m     Document Type: Article

References (76)

1. For reviews on the chemistry, synthesis, and physical properties of acylsilanes, see: (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147. (b) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647. (c) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553.
2. For reviews on the chemistry, synthesis, and physical properties of acylsilanes, see: (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147. (b) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647. (c) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553.
3. For reviews on the chemistry, synthesis, and physical properties of acylsilanes, see: (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147. (b) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647. (c) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553.
4. Brook, A. G. Adv. Organomet. Chem. 1968, 7, 96.
5. Buynak, J. D.; Strickland, J. B.; Hurd, T.; Phan, A. J. Chem. Soc., Chem. Commun. 1989, 89.
6. (a) Yoshida, J.-i.; Itoh, M.; Matsunaga, S.-i.; Isoe, S. J. Org. Chem. 1992, 57, 4877.
7. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E. Tetrahedron Lett. 1990, 31, 6935.
8. For a representive example, see: Reich, H. J.; Eisenhart, E. K.; Olsen, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791.
9. For a representive example, see: Kuwajima, I.; Enda, J. J. Am. Chem. Soc. 1985, 107, 5495.
10. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
11. Reich, H. J.; Eisenhart, E. K. J. Org. Chem. 1984, 49, 5282.
12. Schinzer, D. Synthesis 1989, 179.
13. Honuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353.
14. Ricci, A.; Degl'Innocenti, A; Borselli, G.; Reginato, G. Tetrahedron Lett. 1987, 28, 4093.
15. Degl'Innocenti, A.; Pike, S.; Walton, D. R. M.; Seconi, G.; Ricci, A.; Fiorenza, M. J. Chem. Soc., Chem. Commun. 1980, 1201.
16. Schnizer, D.; Heathcock, C. H. Tetrahedron Lett. 1981, 22, 1881.
17. Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509.
18. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949.
19. Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2513.
20. (a) Dalton, J. C.; Bourque, R. A. J. Am. Chem. Soc. 1981, 103, 699.
21. (b) Harris, J. M.; Macinnes, I.; Walton, J. C.; Mailard, B. J. J. Organometal. Chem. 1991, 403, C25-C28.
22. (c) Tsai, Y.-M.; Cherng, C.-D. Tetrahedron Lett. 1991, 32, 3515.
23. (d) Curran, D. P.; Jiang, W.-T.; Palovich, M.; Tsai, Y.-M. Synlett 1993, 403.
24. (e) Tsai, Y.-M.; Tang, K.-H.; Jiaang, W.-T. Tetrahedron Lett. 1993, 34, 1303.
25. (f) Tsai, Y.-M., Ke, B.-W. J. Chin. Chem. Soc. 1993, 40, 641.
26. (g) Robertson, J.; Burrows, J. N. Tetrahedron Lett. 1994, 35, 3777.
27. (h) Tsai, Y.-M.; Chang, S.-Y. J. Chem. Soc., Chem. Commun. 1995, 981.
28. 2, see: (a) Kagan, H. B; Namy, J. L. Tetrahedron 1986, 42, 6373. (b) Inanaga, J. J. Syn. Org. Chem. 1989, 47, 200. (c) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Brandukova, N. E.; Vygodakii, Y. S.; Vinogradova, S. V. Russ. Chem. Rev. 1994, 63, 345.
29. 2, see: (a) Kagan, H. B; Namy, J. L. Tetrahedron 1986, 42, 6373. (b) Inanaga, J. J. Syn. Org. Chem. 1989, 47, 200. (c) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Brandukova, N. E.; Vygodakii, Y. S.; Vinogradova, S. V. Russ. Chem. Rev. 1994, 63, 345.
30. 2, see: (a) Kagan, H. B; Namy, J. L. Tetrahedron 1986, 42, 6373. (b) Inanaga, J. J. Syn. Org. Chem. 1989, 47, 200. (c) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Brandukova, N. E.; Vygodakii, Y. S.; Vinogradova, S. V. Russ. Chem. Rev. 1994, 63, 345.
31. 2, see: (a) Kagan, H. B; Namy, J. L. Tetrahedron 1986, 42, 6373. (b) Inanaga, J. J. Syn. Org. Chem. 1989, 47, 200. (c) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Brandukova, N. E.; Vygodakii, Y. S.; Vinogradova, S. V. Russ. Chem. Rev. 1994, 63, 345.
32. 2, see: (a) Kagan, H. B; Namy, J. L. Tetrahedron 1986, 42, 6373. (b) Inanaga, J. J. Syn. Org. Chem. 1989, 47, 200. (c) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (d) Molander, G. A. Chem. Rev. 1992, 92, 29. (e) Brandukova, N. E.; Vygodakii, Y. S.; Vinogradova, S. V. Russ. Chem. Rev. 1994, 63, 345.
33. For intermolecular ketyl-olefin coupling reactions, see: Ujikawa, O.; Inanaga, J.; Yamaguchi, M.; Tetrahedron Lett. 1989, 30, 2837
34. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
35. (a) Molander, G. A.; Kenny, C. Tetrahedron Lett. 1987, 28, 4367.
36. (b) Fevig, T. L.; Elliott, R. L.; Curran, D. P. J. Am. Chem. Soc. 1988, 110, 5064.
37. (c) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1991, 56, 4112.
38. (a) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
39. (b) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75.
40. (c) Enholm, E. J.; Burroff, J. A. Tetrahedron Lett. 1992, 33, 1835.
41. (d) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785.
42. (e) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899.
43. (f) Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C. Tetrahedron Lett. 1994, 35, 129.
44. (g) Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1995, 117, 7283.
45. (h) Enholm, E. J.; Kirster, K. S. J. Org. Chem. 1995, 60, 4850.
46. (a) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 431.
47. (b) Corey, E. J.; Seebach, D.; Freedman, R. J. Am. Chem. Soc. 1967, 89, 434.
48. Miller, J. A.; Zweifel, G. Synthesis 1981, 288.
49. Vedejs, E.; Fuchs, P. L. J. Org. Chem. 1971, 36, 366.
50. (a) Ho, T.-L; Ho, H. C.; Wong, C. M. J. Chem. Soc., Chem. Commun. 1972, 791.
51. (b) Ho, H. C.; Ho, T.-L; Wong, C. M. Can. J. Chem. 1972, 50, 2718.
52. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
53. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1077.
54. Kulkarni, S.; Patil, V D. Heterocycles 1982, 18, 163.
55. Tsai, Y.-M.; Nieh, H.-C.; Cherng, C.-D. J. Org. Chem. 1992, 57, 7010.
56. Taniguchi, Y.; Fuji, N.; Makioka, Y.; Takaki, K., Fujiwara, Y. Chem. Lett. 1993, 1165.
57. Shiue, J. S.; Lin, C. C.; Fang, J. M. Tetrahedron Lett. 1993, 34, 335.
58. (a) Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439.
59. (b) Curran, D. P.; Totleben, M. J. Am. Chem. Soc. 1992, 114, 6050.
60. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
61. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
62. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
63. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
64. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
65. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
66. For general radical cyclizations, see: (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959. For O-stannyl ketyl related cyclizations, see: (d) Hon, Y.-S.; Sun, P.-P.; Lu, H.-L.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 445. For O-samarium ketyl related cyclizations, see: (e) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1992, 57, 3132. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. (g) Molander, G. A.: Mckie, J. A. J. Org. Chem. 1995, 60, 872.
67. Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939.
68. 2(Ot-Bu) promoted reaction of 5-oxohexanal, see: Unenishi, J.; Masuda, S.; Wakabayashi. S. Tetrahedron Lett. 1991, 32, 5097.
69. Heathcock, C. H. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford. 1991; Vol. 2, Chap. 1.5.
70. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447 and the references cited therein.
71. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765.
72. (a) Davies, A. G.; Tse, M.-W. J. Organomet. Chem. 1978, 155, 25.
73. (b) Hasegawa, E.; Ishiyama, K.; Kato, T.; Horaguchi, T.; Shimizu, T. J. Org. Chem. 1992, 57, 5352.
74. Giese, B. Angew. Chem., Int. Ed Engl. 1989, 28, 969.
75. Wright, A.; West, R. J. Am. Chem. Soc. 1974, 96, 3220
76. A commercially available compound. Beil. 7 (2), 368.