The study of intramolecular tandem radical cyclizations of acylsilanes with radicalphiles attached on silicon

Tetrahedron

Volumn 61, Issue 8, 2005, Pages 2037-2045

  Tang, Kuo Hsiang ^a   Liao, Fang Yu ^a   Tsai, Yeun Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Acylsilanes; Alkoxysilane; Brook rearrangement; Tandem radical cyclizations

Indexed keywords

ETHER DERIVATIVE; HYDROXYL GROUP; SILANE DERIVATIVE; SILICON;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CYCLIZATION; OXIDATION KINETICS; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 13444280144     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.12.053     Document Type: Article

References (74)

1. J. Fossey, D. Lefort, and J. Sorba Free Radicals in Organic Chemistry 1995 Wiley New York
2. B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K.J. Kulicke, and F. Trach Org. React. 48 1996 301 856
3. P. Renaud M.P. Sibi Radicals in Organic Synthesis 2001 Wiley-VCH Weinheim
4. A.L.J. Beckwith, and B.P. Hay J. Am. Chem. Soc. 111 1989 230 234
5. A.L.J. Beckwith, and B.P. Hay J. Am. Chem. Soc. 111 1989 2674 2681
6. A.L.J. Beckwith, and K.D. Raner J. Org. Chem. 57 1992 4954 4962
7. R. Tsang, J.K. Dickson Jr., H. Pak, R. Walton, and B. Fraser-Reid J. Am. Chem. Soc. 109 1987 3484 3486
8. B. Fraser-Reid, G.D. Vite, B.-W.A. Yeung, and R. Tsang Tetrahedron Lett. 29 1988 1645 1648
9. R. Walton, and B. Fraser-Reid J. Am. Chem. Soc. 113 1991 5791 5799
10. For reviews about ring-expansions initiated by intramolecular radical additions to carbonyl, see: (a) P. Dowd, and W. Zhang Chem. Rev. 93 1993 2091 2115
11. L. Yet Tetrahedron 55 1999 9349 9403
12. (c) Zhang, W. in Ref. 1c, Vol. 2, pp 234-245.
13. W. Zhang Curr. Org. Chem. 6 2002 1015 1029
14. J. Hartung, T. Gottwald, and K. Špehar Synthesis 2002 1469 1498
15. For a review about carbon-oxygen double bonds as radical traps, see: Kim, S.; Yoon, J.-Y. in Ref. 1c, Vol. 2, pp 1-21.
16. D.P. Curran, and H. Liu J. Org. Chem. 56 1991 3463 3465
17. D.P. Curran, and M. Palovich Synlett 1992 631 632
18. D.P. Curran, U. Diederichsen, and M. Palovich J. Am. Chem. Soc. 119 1997 4797 4804
19. U. Diederichsen, and D.P. Curran J. Organomet. Chem. 531 1997 9 12
20. S. Kim, and S.Y. Jon J. Chem. Soc., Chem. Commun. 1996 1335 1336
21. S. Kim, and S.Y. Jon J. Chem. Soc., Chem. Commun. 1998 815 816
22. S. Kim, and S.Y. Jon Tetrahedron Lett. 39 1998 7317 7320
23. R.A. Batey, and D.B. MacKay Tetrahedron Lett. 39 1998 7267 7270
24. S. Kim, and D.H. Oh Synlett 1998 525 527
25. D.L.J. Clive, and M.H.D. Postema J. Chem. Soc., Chem. Commun. 1993 429 430
26. P. Devin, L. Fensterbank, and M. Malacria Tetrahedron Lett. 39 1998 833 836
27. P. Devin, L. Fensterbank, and M. Malacria Tetrahedron Lett. 40 1999 5511 5514
28. M. Chareyron, P. Devin, L. Fensterbank, and M. Malacria Synlett 2000 83 85
29. D.S. Hays, and G.C. Fu J. Am. Chem. Soc. 117 1995 7283 7284
30. D.S. Hays, and G.C. Fu J. Org. Chem. 63 1998 6375 6381
31. S.-Y. Chang, Y.-F. Shao, S.-F. Chu, G.-T. Fan, and Y.-M. Tsai Org. Lett. 1 1999 945 948
32. Y.-M. Tsai, and C.-D. Cherng Tetrahedron Lett. 32 1991 3515 3518
33. Y.-M. Tsai, K.-H. Tang, and W.-T. Jiaang Tetrahedron Lett. 34 1993 1303 1306
34. D.P. Curran, W.-T. Jiaang, M. Palovich, and Y.-M. Tsai Synlett 1993 403 404
35. Y.-M. Tsai, and S.-Y. Chang J. Chem. Soc., Chem. Commun. 1995 981 982
36. T.-H. Chuang, J.-M. Fang, W.-T. Jiaang, and Y.-M. Tsai J. Org. Chem. 61 1996 1794 1805
37. Y.-M. Tsai, K.-H. Tang, and W.-T. Jiaang Tetrahedron Lett. 37 1996 7767 7770
38. Y.-M. Tsai, H.-C. Nieh, J.-S. Pan, and D.-D. Hsiao J. Chem. Soc., Chem. Commun. 1996 2469 2470
39. S.-Y. Chang, W.-T. Jiaang, C.-D. Cherng, K.-H. Tang, C.-H. Huang, and Y.-M. Tsai J. Org. Chem. 62 1997 9089 9098
40. W.-T. Jiaang, H.-C. Lin, K.-H. Tang, L.-B. Chang, and Y.-M. Tsai J. Org. Chem. 64 1999 618 628
41. C.-H. Huang, S.-Y. Chang, N.-S. Wang, and Y.-M. Tsai J. Org. Chem. 66 2001 8983 8991
42. For recent reviews about acylsilanes, see: (a) A. Ricci, and A. Degl'Innocenti Synthesis 1989 647 660
43. P.C.B. Page, S.S. Klair, and S. Rosenthal Chem. Soc. Rev. 19 1990 147 195
44. P.F. Cirillo, and J.S. Panek Org. Prep. Proc. Int. 24 1992 553 582
45. P.C.B. Page, M.J. McKenzie, S.S. Klair, and S. Rosenthal Z. Rappoport Y. Apeloig The Chemistry of Organic Silicon Compounds Vol. 2 1998 Wiley New York 1599 1665 Chapter 27
46. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci J. Organomet. Chem. 567 1998 181 189
47. For a recent review about Brook rearrangement, see: W.H. Moser Tetrahedron 57 2001 2065 2084
48. J.C. Dalton, and R.A. Bourque J. Am. Chem. Soc. 103 1981 699 700
49. J.M. Harris, I. MacInnes, J.C. Walton, and B. Maillard J. Organomet. Chem. 403 1991 C25 C28
50. Y.-M. Tsai, and B.-W. Ke J. Chin. Chem. Soc. (Taipei) 40 1993 641 642
51. J. Robertson, and J.N. Burrows Tetrahedron Lett. 35 1994 3777 3780
52. C.H. Schiesser, and M.L. Styles J. Chem. Soc., Perkin Trans. 2 1997 2335 2340
53. M.D. Paredes, and R. Alonso Tetrahedron Lett. 40 1999 3973 3976
54. M.D. Paredes, and R.J. Alonso Org. Chem. 65 2000 2292 2304
55. K. Tamao G.L. Larson Advances in Silicon Chemistry Vol. 3 1996 Jai Greenwich CT 1 62
56. G.R. Jones, and Y. Landais Tetrahedron 52 1996 7599 7662
57. A.G. Brook, J.M. Duff, P.F. Jones, and N.R. Davis J. Am. Chem. Soc. 89 1967 431 434
58. E.J. Corey, D. Seebach, and R. Freedman J. Am. Chem. Soc. 89 1967 434 436
59. G. Stork, and P.F. Keitz Tetrahedron Lett. 30 1989 6981 6984
60. J. Robertson, G. O'Connor, T. Sardharwala, and D.S. Middleton Tetrahedron 56 2000 8309 8320
61. J. Robertson, G. O'Connor, C.L. Ringrose, and D.S. Middleton Tetrahedron 56 2000 8321 8333
62. T.-L. Ho, H.C. Ho, and C.M. Wong J. Chem. Soc., Chem. Commun. 1972 791 791
63. H.C. Ho, T.-L. Ho, and C.M. Wong Can. J. Chem. 50 1972 2718 2721
64. G. Stork, and K. Zhao Tetrahedron Lett. 30 1989 287 290
65. K. Tamao, N. Ishida, T. Tanaka, and M. Kumada Organometallics 2 1983 1694 1696
66. J.W. Wilt, J. Lusztyk, M. Peeran, and K.U. Ingold J. Am. Chem. Soc. 110 1988 281 287
67. J.W. Wilt Tetrahedron 41 1985 3979 4000
68. A.G. Myers, D.Y. Gin, and D.H. Rogers J. Am. Chem. Soc. 116 1994 4697 4718
69. A.L.J. Beckwith, I.A. Blair, and G. Phillipou Tetrahedron Lett. 26 1974 2251 2254
70. A.L.J. Beckwith Tetrahedron 37 1981 3073 3100
71. A.de. Meijere, D. Faber, U. Heinecke, R. Walsh, T. Müller, and Y. Apeloig Eur. J. Org. Chem. 2001 663 680
72. A. Fürstner, and D. Voigtländer Synthesis 2000 959 969
73. P. Canonne, G.B. Foscolos, and D. Bélanger J. Org. Chem. 45 1980 1828 1835
74. H. Shimizu, Y. Shimada, A. Tomita, and O. Mitsunobu Tetrahedron Lett. 38 1997 849 852