Stereoselective hydrogen transfer reactions of vinyl radicals: Cyclization of alkynyl iodides by unimolecular chain transfer from silicon hydrides

Tetrahedron

Volumn 53, Issue 16, 1997, Pages 5679-5698

  Martinez Grau, Angeles ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030904327     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00257-3     Document Type: Article

References (69)

1. a) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969;
2. b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
3. b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139.
4. c) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: Weinheim, 1996, pp 283.
5. a) Choi, J.-K.; Hart, D. J.; Tsai, Y.-M. Tetrahedron Lett. 1982, 4765;
6. b) Stork, G.; Mook, R. Jr. J. Am. Chem. Soc. 1983, 105, 3720;
7. c) Lowinger, T. B.; Weiler, L. J. Org. Chem. 1992, 57, 6099;
8. d) Pradhan, S. K.; Sitabkhan, S. Tetrahedron Lett. 1993, 34, 5615;
9. e) Journet, M.; Magnol, E.; Smadja, W.; Malacria, M. Synlett 1991, 58;
10. f) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
11. a) Metzger, J. O.; Blumenstein, M. Chem. Ber. 1993, 126, 2493;
12. b) Metzger, J. O.; Bangert, F. Chem. Ber. 1994, 127, 673.
13. Iodine atom transfer cyclizations: a) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489;
14. b) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1989, 111, 6265;
15. c) Curran, D. P.; Chen, M.-H. J. Am. Chem. Soc. 1987, 109, 6558;
16. d) Haaima, G.; Lynch, M.-J.; Routledge, A.; Weavers, R. T. Tetrahedron 1993, 49, 4229.
17. Iodine atom transfer additions: a) Curran, D. P.; Kim, D. Tetrahedron 1991, 47, 6171;
18. b) Curran, D. P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189.
19. Chatgilialoglu, C.; Ferreri, C. In Chemistry of Functional Groups, Supplement C2; S. Patai, Ed.; John Wiley & Sons Ltd: Baffins Lane, Chichester, United Kingdom PO19 7UD, 1994; pp 917.
20. Jenkins, P. R.; Symons, M. C. R.; Booth, S. E.; Swain, C.J. Tetrahedron Lett. 1992, 33, 3543.
21. Giese, B.; Lachhein, S. Angew. Chem. Int. Ed. Engl. 1982, 21, 768.
22. Giese, B.; Gonzalez-Gomez, J. A.; Lachhein, S.; Metzger, J.O. Angew. Chem. Int. Ed. Engl. 1987, 26, 479.
23. a) Ferreri, C.; Ballestri, M.; Chatgilialoglu, C. Tetrahedron Lett. 1993, 34, 5147;
24. b) Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826.
25. A few cases of 1,4 and 1,6-hydrogen atom transfer have been reported: a) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893;
26. b) Bennett, S. M.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1986, 878;
27. c) Clive, D. L. J.; Khodabocus, A.; Cantin, M.; Tao, Y. J. Chem. Soc., Chem. Commun. 1991, 1755.
28. a) Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900;
29. b) Curran, D.P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051;
30. c) Bogen, S.; Journet, M.; Malacria, M. Synlett 1994, 958.
31. Giese, B.; Dupuis, J.; Hasskerl, T.; Meixner, J. Tetrahedron Lett. 1983, 24, 703.
32. a) Curran, D. P.; Xu, J.; Lazzarini, E. J. Am. Chem. Soc. 1995, 117, 6603;
33. b) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049.
34. Curran, D. P.; Xu, J. J. Chem. Soc., Perkin Trans. 1 1995, 3061.
35. Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332.
36. a) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595;
37. b) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137.
38. c) Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245.
39. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1982, 104, 5123.
40. There are some exceptions to this generalization, including the reduction of xanthates by silicon hydrides and thiol catalyzed reductions. For a review about structural and chemical properties of silyl radicals, see: Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229.
41. a) Clive, D. L. J.; Cantin, M. J. Chem. Soc., Chem. Commun. 1995, 319;
42. b) Clive, D. L. J.; Yang, W. J. Chem. Soc., Chem. Commun. 1996, 1605.
43. Barton, T. J.; Revis, A. J. Am. Chem. Soc. 1984, 106, 3802.
44. Brown, S.; Ley, S. V.; Vile, S.; Thompson, M. Tetrahedron 1991, 47, 1329.
45. Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron 1991, 47, 4879.
46. Uesato, S.; Kobayashi, K.; Inouye, H. Chem. Pharm. Bull. 1982, 30, 927.
47. Nishitani, K.; Nakamura, Y.; Orii, R.; Arai, Ch.; Yamakawa, K. Chem. Pharm. Bull. 1993, 41, 822.
48. Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396.
49. a) Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 99;
50. b) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 6190.
51. Schmidt, S. P.; Brooks, D. W. Tetrahedron Lett. 1987, 28, 767.
52. One possibilty is that the product 40 is formed, but that it is unstable. Compound 40 contains both a silicon iodide and an alcohol which is tertiary and is the precursor of a highly conjugated cation. This functionality may not be compatible.
53. This crystal structure is one of the first of an alkoxy silicon iodide, and its details will be reported separately. Martinez-Grau, A.; Curran, D. P.; Gieb, S., manuscript in preparation.
54. Sanghvi, Y. S.; Rao, A. S. J. Heterocyclic Chem. 1984, 21, 317.
55. a) Peijnenburg, W. J. G. M.; Buck, H. M. Tetrahedron 1988, 44, 4927;
56. b) Costantino, P.; Crotti, P.; Ferretti, M.; Macchia, F. J. Org. Chem. 1982, 47, 2917.
57. Trost, B. M.; Latimer, L. H. J. Org. Chem. 1978, 43, 1031.
58. a) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521;
59. b) Battioni, J. P.; Capmau, M. L.; Chodkiewicz, W. Bull. Soc. Chim. Fr. 1969, 976.
60. a) Bennet, J. E.; Howard, J. A. Chem. Phys. Lett. 1971, 9, 460;
61. b) Neilson, G. W.; Symons, M. C. R. J. Chem. Soc., Perkin Trans. 2 1973, 1405;
62. c) Ito, O.; Omori, R.; Matsuda, M. J. Am. Chem. Soc. 1982, 104, 3934.
63. a) Kopchik, R. M.; Kampmeier, J. A. J. Am. Chem. Soc. 1968, 90, 6733;
64. b) Singer, L. A.; Chen, J. Tetrahedron Lett. 1969, 4849.
65. Kagel, J. R.; Mertes, M. P. J.Org. Chem. 1987, 52, 2950.
66. Larson, G. L.; Prieto, J. A.; Hernandez, A. Tetrahedron Lett. 1981, 22, 1575.
67. Tanikaga, R.; Nozaki, Y.; Nishida, M.; Kaji, A. Bull. Chem. Soc. Jpn. 1984, 57, 729.
68. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
69. Olah, G. A.; Prakash, G. K. S.; Krishnamurti, R. In Advances in Silicon Chemistry, Vol 1; G. L. Larson, Ed.; J a I Press Ine: 55 Old Post Road, No 2, PO Box 1678, Greenwich, CT 06836-1678, 1991; Vol. 1; pp 1.