The first radical method for the introduction of an ethynyl group using a silicon tether and its application to the synthesis of 2′-deoxy-2′-C-ethynylnucleosides

Journal of Organic Chemistry

Volumn 68, Issue 9, 2003, Pages 3465-3475

  Sukeda, Makoto ^a   Ichikawa, Satoshi ^a   Matsuda, Akira ^a   Shuto, Satoshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL METHODS;

METABOLITES; SYNTHESIS (CHEMICAL); TOLUENE;

SILICON;

2 IODOINDANOL [2 (TRIMETHYLSILYL)ETHYNYL]DIMETHYLSILYL ETHER; 2' DEOXY 2' C ETHYNYLCYTIDINE; 2' DEOXY 2' C ETHYNYLNUCLEOSIDE DERIVATIVE; 2' DEOXY 2' C ETHYNYLURIDINE; ETHER; ETHYNYLDIMETHYLSILYL; INDAN DERIVATIVE; NUCLEOSIDE DERIVATIVE; SILANE DERIVATIVE; SILICON; TETRABUTYLAMMONIUM; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELIMINATION REACTION; ION TRANSPORT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CHEMISTRY, ORGANIC; CYCLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEOSIDES; SILICON; STEREOISOMERISM;

EID: 0037414497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0206667     Document Type: Article

References (129)

1. This publication constitutes Part 219 of the series Nucleosides and Nucleotides: for Part 218 see: Ueno, Y.; Hoshika, S.; Shibata, A.; Jin, J.; Kitade, Y.; Matsuda, A. Bioorg. Med. Chem. Submitted for publication.
2. (a) Goldzieher, J. W.; Brody, S. A. Am. J. Obstet. Gynecol. 1990, 163, 2114-2119.
3. (b) Takeo, S. Cardiovasc. Drug Rev. 1992, 10, 392-403.
4. (c) Anton, S. Ann. N.Y. Acad. Sci. 1988, 544, 46-2.
5. (a) Kando, J. C.; Kalunian, D. A. Hosp. Formul. 1990, 25, 849-850.
6. (b) Harada, S.; Takayama, S. Yakuri to Chiryo 1991, 19, S789-S795.
7. (c) Graul, A.; Rabasseda, X.; Castaner, J. Drugs Future 1998, 23, 133-141.
8. (a) Freidrich, K. The Chemistry of Triple-Bonded Functional Groups. In The Chemistry of Functional Groups, Supplement C; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; p 1380.
9. (b) Brandsma, L. Preparative Acetylene Chemistry, 2nd ed.; Elsevier: Amsterdam, The Netherlands, 1988.
10. (c) Jones, A. M.; Stanforth, S. P. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Sainsbury, M., Ed.; Elsevier: Amsterdam, The Netherlands, 1991; Suppl. 2, 1A/B, p 156.
11. (d) Furber, M. Alkynes. In Comprehensive Organic Functional Group Transformations; Roberts, S. M., Ed.; Cambridge University Press: Cambridge, UK, 1995; pp 998-1085.
12. Sukeda, M.; Shuto, S.; Sugimoto, I.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 8988-8996 and references therein.
13. (a) Matsuda, A.; Minakawa, N.; Sasaki, T.; Ueda, T. Chem. Pharm. Bull. 1988, 36, 2730-2733.
14. (b) Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778-786.
15. (c) De Clercq, E.; Cools, M.; Balzarini, J.; Snoeck, R.; Andrei, G.; Hosoya, M.; Shigeta, S.; Ueda, T.; Minakawa, N.; Matsuda, A. Antimicrob. Agents Chemother. 1991, 679-684.
16. (d) Shigeta, S.; Mori, S.; Baba, M.; Ito, M.; Honzumi, K.; Nakamura, K.; Oshitani, H.; Numazaki, Y.; Matsuda, A.; Obara, T.; Shuto, S.; De Clercq, E. Antimicrob. Agents Chemother. 1992, 36, 435-439.
17. (e) Minakawa, N.; Matsuda, A. Curr. Med. Chem. 1999, 6, 615-628.
18. (a) Matsuda, A.; Hattori, H.; Tanaka, M.; Sasaki, T. Bioorg. Med. Chem. Lett. 1996, 6, 1887-1892.
19. (b) Tabata, S.; Tanaka, M.; Matsuda, A.; Fukushima, M.; Sasaki, T. Oncol. Rep. 1996, 3, 1029-1034.
20. (c) Hattori, H.; Tanaka, M.; Fukushima, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1996, 39, 5005-5011.
21. (d) Hattori, H.; Nozawa, E.; Iino, T.; Yoshimura, Y.; Shuto, S.; Shimamoto, M.; Nomura, Y.; Fukushima, M.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1998, 41, 2892-2902.
22. (e) Takatori, S.; Kanda, H.; Takenaka, K.; Wataya, Y.; Matsuda, A.; Fukushima, M.; Shimamoto, Y.; Tanaka, M.; Sasaki, T. Cancer Chemother. Pharmacol. 1999, 44, 97-104.
23. (a) Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385-388.
24. (b) Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matsuda, A. J. Med. Chem. 1999, 42, 2901-2908.
25. (c) Ohrui, H.; Kohgo, S.; Kitano, K.; Sakata, S.; Kodama, E.; Yoshimura, K.; Matsuoka, M.; Shigeta, S.; Mitsuya, H. J. Med. Chem. 2000, 43, 4516-4525.
26. (d) Kodama, E. I.; Kohgo, S.; Kitano, K.; Machida, H.; Gatanaga, H.; Shigeta, S.; Matsuoka, M.; Ohrui, H.; Mitsuya, H. Antimicrob. Agents Chemother. 2001, 45, 1539-1546.
27. (a) Abiru, T.; Yamaguchi, T.; Watanabe, Y.; Kogi, K.; Matsuda, A. Eur. J. Pharmacol. 1991, 196, 69-76.
28. (b) Matsuda, A.; Shinozaki, M.; Yamaguchi, T.; Homma, H.; Nomoto, R.; Miyasaka, T.; Watanabe, Y.; Abiru, T. J. Med. Chem. 1992, 35, 241-252.
29. (c) Abiru, T.; Miyashita, T.; Watanabe, Y.; Yamaguchi, T.; Matsuda, A. J. Med. Chem. 1992, 35, 2253-2260.
30. (d) Homma, H.; Watanabe, Y.; Abiru, T.; Murayama, T.; Nomura, Y.; Matsuda, A. J. Med. Chem. 1992, 35, 2881-2890.
31. (a) Matsuda, A.; Kosaki, H.; Yoshimura, Y.; Shuto, S.; Ashida, N.; Shigeta, S. Bioorg. Med. Chem. Lett. 1995, 5, 1685-1688.
32. (b) Matsuda, A.; Kosaki, H.; Saitoh, Y.; Yoshimura, Y.; Minakawa, N.; Nakata, H. J. Med. Chem. 1998, 41, 2676-2678.
33. (c) Yoshioka, K.; Matsuda, A.; Nakata, H. Clin. Exp. Pharmcol. Physiol. 2001, 28, 278-284.
34. (d) Shinozuka, K.; Ishii-Nozawa, R.; Takeuchi, K.; Minakawa, N.; Matsuda, A.; Nakata, H.; Kunitomo, M. Clin. Exp. Pharmacol. Physiol. 2001, 28, 312-314.
35. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
36. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
37. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
38. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
39. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
40. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
41. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
42. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
43. Alkynes are also prepared by functional group transformations forming C≡C bonds, for examples see: (a) Bottini, A. T.; King, B. J.; Lucas, J. M. J. Org. Chem. 1962, 27, 3688-3690. (b) Okuhara, K. J. Org. Chem. 1976, 41, 1487-1494. (c) Negishi, E.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526-2528. (d) Shibasaki, M.; Torisawa, Y.; Ikegami, S. Tetrahedron Lett. 1982, 23, 4607-4610. (e) Tsuji, J.; Kezuka, H.; Toshida, Y.; Takayanagi, H.; Yamamoto, K. Tetrahedron 1983, 39, 3279-3282. (f) Ochiai, M.; Sumi, K.; Nagao, Y.; Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc., Chem. Commun. 1985, 697-699. (g) Abidi, S. L. Tetrahedron Lett. 1986, 27, 267-270. (h) Akiyama, S.; Nakatsuji, S.; Nomura, K.; Matsuda, K.; Nakashima, K. J. Chem. Soc., Chem. Commun. 1991, 948-950. (i) Ireland, R. E.; Highsmith, T. K.; Genas, L. D.; Gleason, J. L. J. Org. Chem. 1992, 57, 5071-5073.
44. Reactions of acetylides, for examaples see: (a) Smith, W. N.; Beumel, O. F., Jr. Synthesis 1974, 441-442. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236. (c) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577-1582. (d) Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990, 31, 5499-5502. (e) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
45. Reactions of acetylides, for examaples see: (a) Smith, W. N.; Beumel, O. F., Jr. Synthesis 1974, 441-442. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236. (c) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577-1582. (d) Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990, 31, 5499-5502. (e) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
46. Reactions of acetylides, for examaples see: (a) Smith, W. N.; Beumel, O. F., Jr. Synthesis 1974, 441-442. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236. (c) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577-1582. (d) Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990, 31, 5499-5502. (e) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
47. Reactions of acetylides, for examaples see: (a) Smith, W. N.; Beumel, O. F., Jr. Synthesis 1974, 441-442. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236. (c) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577-1582. (d) Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990, 31, 5499-5502. (e) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
48. Reactions of acetylides, for examaples see: (a) Smith, W. N.; Beumel, O. F., Jr. Synthesis 1974, 441-442. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236. (c) Brown, H. C.; Molander, G. A.; Singh, S. M.; Racherla, U. S. J. Org. Chem. 1985, 50, 1577-1582. (d) Isobe, M.; Hirose, Y.; Shimokawa, K.; Nishikawa, T.; Goto, T. Tetrahedron Lett. 1990, 31, 5499-5502. (e) Meyers, A. I.; Bienz, S. J. Org. Chem. 1990, 55, 791-798.
49. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
50. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
51. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
52. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
53. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
54. Cross-coupling reactions introducing ethynyl groups, for examples see: (a) Armitage, J. B.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1952, 2014-2018. (b) Gardner, J. N.; Jones, E. R. H.; Leeming, P. R.; Stephenson, J. S. J. Chem. Soc. 1960, 691-697. (c) Giacomelli, G.; Marcacci, F.; Caporusso, A. M.; Lardicci, L. Tetrahedron Lett. 1979, 20, 3217-3220. (d) Okuhara, K. Bull. Chem. Soc. Jpn. 1981, 54, 2045-2052. (e) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866. (f) Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1990, 55, 63-69.
55. Reactions of alkynylhalides, for examples see: (a) Oliver, R.; Walton, D. R. M. Tetrahedron Lett. 1972, 13, 5209-5212. (b) Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465-1468. (c) Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551-3562. (d) de Graaf, W.; Smits, A.; Boersma, J.; van Koten, G. Tetrahedron 1988, 44, 6699-6704. (e) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799-4802.
56. Reactions of alkynylhalides, for examples see: (a) Oliver, R.; Walton, D. R. M. Tetrahedron Lett. 1972, 13, 5209-5212. (b) Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465-1468. (c) Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551-3562. (d) de Graaf, W.; Smits, A.; Boersma, J.; van Koten, G. Tetrahedron 1988, 44, 6699-6704. (e) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799-4802.
57. Reactions of alkynylhalides, for examples see: (a) Oliver, R.; Walton, D. R. M. Tetrahedron Lett. 1972, 13, 5209-5212. (b) Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465-1468. (c) Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551-3562. (d) de Graaf, W.; Smits, A.; Boersma, J.; van Koten, G. Tetrahedron 1988, 44, 6699-6704. (e) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799-4802.
58. Reactions of alkynylhalides, for examples see: (a) Oliver, R.; Walton, D. R. M. Tetrahedron Lett. 1972, 13, 5209-5212. (b) Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465-1468. (c) Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551-3562. (d) de Graaf, W.; Smits, A.; Boersma, J.; van Koten, G. Tetrahedron 1988, 44, 6699-6704. (e) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799-4802.
59. Reactions of alkynylhalides, for examples see: (a) Oliver, R.; Walton, D. R. M. Tetrahedron Lett. 1972, 13, 5209-5212. (b) Normant, J. F.; Commercon, A.; Villieras, J. Tetrahedron Lett. 1975, 16, 1465-1468. (c) Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551-3562. (d) de Graaf, W.; Smits, A.; Boersma, J.; van Koten, G. Tetrahedron 1988, 44, 6699-6704. (e) Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 4799-4802.
60. (a) Laird, E. E.; Jorgensen, W. L. J. Org. Chem. 1990, 55, 9-27.
61. (b) Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385-1489.
62. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
63. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 4, pp 715-831.
64. (e) Motherwell, W. B.; Crich, D. Free-Radical Chain Reactions in Organic Synthesis; Academic Press: London, UK, 1992.
65. (f) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of radical reactions; VCH: Weinheim, Germany, 1996.
66. (g) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856.
67. (h) Renaud, P.; Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001.
68. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
69. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
70. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
71. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
72. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
73. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
74. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
75. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
76. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
77. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
78. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
79. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
80. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
81. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
82. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
83. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
84. Radical reactions with silicon tethers, for examples see: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetraheron Lett. 1991, 32, 573-576. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetraherdon Lett. 1991, 32, 401-404. (k) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58, 349-370. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (p) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394. (q) Abe, H.; Shuto, S.; Matsuda, A. J. Org. Chem. 2000, 65, 4315-4325.
85. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
86. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
87. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
88. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
89. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
90. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
91. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
92. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
93. Our studies on the radical reactions with a silicon tether: (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667. (d) Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531. (f) Sugimoto, I.; Shuto, S.; Matsuda, A. Synlett 1999, 1766-1768. (g) Shuto, S.; Sugimoto, I.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 1343-1351. (h) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557. (i) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
94. Atom-transfer radical cyclization reaction was first reported by Curran: Curran, D. P.; Cheng, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489-2490.
95. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
96. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5,
97. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
98. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
99. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
100. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
101. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
102. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
103. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
104. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
105. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
106. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
107. Atom-transfer radical cyclization reactions, for examples see: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210. (b) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045. (c) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480. (d) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088. (e) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678. (f) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831. (g) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740. (h) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354- 356. (i) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (j) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960. (k) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Assmetry 1994, 5, 199-202. (l) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1996, 60, 8332-8333. (m) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
108. A preliminary account of this study: Sukeda, M.; Ichikawa, S.; Matsuda, A.; Shuto, S. Angew. Chem., Int. Ed. 2002, 41, 4748-4750.
109. Radical cyclization reactions with a TEDMS group as a tether have been reported: (a) Xi, Z.; Rong, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 5255-5272. (b) Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Doisneau, G.; Riche, C.; Chiaroni, A.; Beau, J.-M. Chem. Eur. J. 1997, 3, 1342-1356.
110. Radical cyclization reactions with a TEDMS group as a tether have been reported: (a) Xi, Z.; Rong, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 5255-5272. (b) Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Doisneau, G.; Riche, C.; Chiaroni, A.; Beau, J.-M. Chem. Eur. J. 1997, 3, 1342-1356.
111. Atom-transfer radical cyclization reactions to a C≡C bond: (a) Curran, D. P.; Chen, M. H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489-2490. (b) Ichinose, Y.; Matsunaga, S.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155-3158.
112. Atom-transfer radical cyclization reactions to a C≡C bond: (a) Curran, D. P.; Chen, M. H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489-2490. (b) Ichinose, Y.; Matsunaga, S.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155-3158.
113. Atom transfer radical reactions effectively occur via a homolytic C-I bond cleavage, see: (a) Curran, D. P.; Kim, D. Tetrahedron Lett. 1986, 27, 5821-5824. (b) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477-2480. (c) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604-8605.
114. Atom transfer radical reactions effectively occur via a homolytic C-I bond cleavage, see: (a) Curran, D. P.; Kim, D. Tetrahedron Lett. 1986, 27, 5821-5824. (b) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477-2480. (c) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604-8605.
115. Atom transfer radical reactions effectively occur via a homolytic C-I bond cleavage, see: (a) Curran, D. P.; Kim, D. Tetrahedron Lett. 1986, 27, 5821-5824. (b) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477-2480. (c) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604-8605.
116. Atom transfer radical reactions effectively occur via a homolytic C-I bond cleavage, see: (a) Curran, D. P.; Kim, D. Tetrahedron Lett. 1986, 27, 5821-5824. (b) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477-2480. (c) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604-8605.
117. Radical atom transfer reactions occur via a homolytic C-Se bond cleavage when a phenylseleno group is attached at a benzylic position: ref 17d
118. Fluoride ion promoted elimination of 2-halogenovinylsilines to produce alkynes has been reported: (a) Yamaguchi, R.; Kawasaki, H.; Yoshitome, T.; Kawanishi H. Chem. Lett. 1982, 1485-1486. (b) Shakespeare, W. C.; Johnson, R. P. J. Am. Chem. Soc. 1990, 112, 8578-8579. (c) Schmitz, C.; Rouanet-Dreyfuss, A.-C.; Tueni, M.; Biellmann, J.-F. J. Org. Chem. 1996, 61, 1817-1821. (d) Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630-633.
119. Fluoride ion promoted elimination of 2-halogenovinylsilines to produce alkynes has been reported: (a) Yamaguchi, R.; Kawasaki, H.; Yoshitome, T.; Kawanishi H. Chem. Lett. 1982, 1485-1486. (b) Shakespeare, W. C.; Johnson, R. P. J. Am. Chem. Soc. 1990, 112, 8578-8579. (c) Schmitz, C.; Rouanet-Dreyfuss, A.-C.; Tueni, M.; Biellmann, J.-F. J. Org. Chem. 1996, 61, 1817-1821. (d) Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630-633.
120. Fluoride ion promoted elimination of 2-halogenovinylsilines to produce alkynes has been reported: (a) Yamaguchi, R.; Kawasaki, H.; Yoshitome, T.; Kawanishi H. Chem. Lett. 1982, 1485-1486. (b) Shakespeare, W. C.; Johnson, R. P. J. Am. Chem. Soc. 1990, 112, 8578-8579. (c) Schmitz, C.; Rouanet-Dreyfuss, A.-C.; Tueni, M.; Biellmann, J.-F. J. Org. Chem. 1996, 61, 1817-1821. (d) Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630-633.
121. Fluoride ion promoted elimination of 2-halogenovinylsilines to produce alkynes has been reported: (a) Yamaguchi, R.; Kawasaki, H.; Yoshitome, T.; Kawanishi H. Chem. Lett. 1982, 1485-1486. (b) Shakespeare, W. C.; Johnson, R. P. J. Am. Chem. Soc. 1990, 112, 8578-8579. (c) Schmitz, C.; Rouanet-Dreyfuss, A.-C.; Tueni, M.; Biellmann, J.-F. J. Org. Chem. 1996, 61, 1817-1821. (d) Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630-633.
122. Formyl group-transfer or cyano group-transfer radical reactions have been reported: (a) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J. L. Synthesis 1995, 1368-1370. (b) Jung, M. E.; Tina, C. S. W. Tetrahedron Lett. 1993, 34, 6247-6250.
123. Formyl group-transfer or cyano group-transfer radical reactions have been reported: (a) Cossy, J.; Poitevin, C.; Pardo, D. G.; Peglion, J. L. Synthesis 1995, 1368-1370. (b) Jung, M. E.; Tina, C. S. W. Tetrahedron Lett. 1993, 34, 6247-6250.
124. Stork, G.; Keitz, P. F. Tetrahedron Lett. 1989, 30, 6981-6984.
125. The cis-stereochemistry was determined by NOE experiments: see Experimental Section.
126. 3B was used under argon, it effectively promoted the atom-transfer radical cyclization reactions of 10a.
127. When the reaction was carried out under oxygen or air, the yield significantly decreased.
128. Shinohara, N.; Arai, M.; Ichinohe, S. JP-52065226, 1977 (Chem. Abstr. 1977, 87, P 135905r).
129. 1H NMR coupling constant: see Experimental Section.