Triethylborane induced radical reaction of gallium enolates with α-halo esters

Bulletin of the Chemical Society of Japan

Volumn 75, Issue 9, 2002, Pages 2049-2052

  Usugi, Shin ichi ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS;

RADICAL INITIATOR;

GALLIUM;

BORANE DERIVATIVE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; GALLIUM; GALLIUM TRICHLORIDE; LITHIUM DERIVATIVE; METHYLLITHIUM; TRIETHYLBORANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLOADDITION; INFRARED SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

EID: 0036393631     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.75.2049     Document Type: Article

References (28)

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4. For triethylborane as a radical initiator, see: a) K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 109, 2547 (1987). (b) K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 39, 923 (1989). (c) K. Oshima and K. Utimoto, J. Syn. Org. Chem., Jpn., 47, 40 (1989). (d) H. Yorimitsu and K. Oshima, "Radicals in Organic Synthesis," ed by P. Renaud and M. P. Sibi, WILEY-VCH, Weinheim (2001), Vol. 1, Chap. 1.2, p. 11. (e) C. Ollivier and P. Renaud, Chem. Rev., 101, 3415 (2001).
5. For triethylborane as a radical initiator, see: a) K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 109, 2547 (1987). (b) K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 39, 923 (1989). (c) K. Oshima and K. Utimoto, J. Syn. Org. Chem., Jpn., 47, 40 (1989). (d) H. Yorimitsu and K. Oshima, "Radicals in Organic Synthesis," ed by P. Renaud and M. P. Sibi, WILEY-VCH, Weinheim (2001), Vol. 1, Chap. 1.2, p. 11. (e) C. Ollivier and P. Renaud, Chem. Rev., 101, 3415 (2001).
6. For triethylborane as a radical initiator, see: a) K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 109, 2547 (1987). (b) K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 39, 923 (1989). (c) K. Oshima and K. Utimoto, J. Syn. Org. Chem., Jpn., 47, 40 (1989). (d) H. Yorimitsu and K. Oshima, "Radicals in Organic Synthesis," ed by P. Renaud and M. P. Sibi, WILEY-VCH, Weinheim (2001), Vol. 1, Chap. 1.2, p. 11. (e) C. Ollivier and P. Renaud, Chem. Rev., 101, 3415 (2001).
7. For triethylborane as a radical initiator, see: a) K. Nozaki, K. Oshima, and K. Utimoto, J. Am. Chem. Soc., 109, 2547 (1987). (b) K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 39, 923 (1989). (c) K. Oshima and K. Utimoto, J. Syn. Org. Chem., Jpn., 47, 40 (1989). (d) H. Yorimitsu and K. Oshima, "Radicals in Organic Synthesis," ed by P. Renaud and M. P. Sibi, WILEY-VCH, Weinheim (2001), Vol. 1, Chap. 1.2, p. 11. (e) C. Ollivier and P. Renaud, Chem. Rev., 101, 3415 (2001).
8. For reactions involving gallium enolates, see: a) M. Yamaguchi, T. Tsukagoshi, and M. Arisawa, J. Am. Chem. Soc., 121, 4074 (1999). (b) Y. Han and Y. Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
9. For reactions involving gallium enolates, see: a) M. Yamaguchi, T. Tsukagoshi, and M. Arisawa, J. Am. Chem. Soc., 121, 4074 (1999). (b) Y. Han and Y. Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
10. 3B-catalyzed radical reactions with α-halo carbonyl compounds, see: a) T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Synlett, 1998, 1351. (b) H. Yorimitsu, K. Wakabayashi, H. Shinokubo, and K. Oshima, Bull. Chem. Soc. Jpn., 74, 1963 (2001). (c) H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto, and H. Fujimoto, J. Am. Chem. Soc., 122, 11041 (2000).
11. 3B-catalyzed radical reactions with α-halo carbonyl compounds, see: a) T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Synlett, 1998, 1351. (b) H. Yorimitsu, K. Wakabayashi, H. Shinokubo, and K. Oshima, Bull. Chem. Soc. Jpn., 74, 1963 (2001). (c) H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto, and H. Fujimoto, J. Am. Chem. Soc., 122, 11041 (2000).
12. 3B-catalyzed radical reactions with α-halo carbonyl compounds, see: a) T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Synlett, 1998, 1351. (b) H. Yorimitsu, K. Wakabayashi, H. Shinokubo, and K. Oshima, Bull. Chem. Soc. Jpn., 74, 1963 (2001). (c) H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto, and H. Fujimoto, J. Am. Chem. Soc., 122, 11041 (2000).
13. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
14. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
15. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
16. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
17. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
18. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
19. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
20. For radical reactions of metal enolates, see: a) K. Miura, N. Fujisawa, H. Saito, D. Wang, and A. Hosomi, Org. Lett., 3, 4055 (2001). (b) G. A. Russell and L. L. Herold, J. Org. Chem., 50, 1037 (1985). (c) Y. Watanabe, T. Yoneda, Y. Ueno, and T. Toru, Tetrahedron Lett., 31, 6669 (1990). (d) K. Miura, M. Taniguchi, K. Nozaki, K. Oshima, and K. Utimoto, Tetrahedron Lett., 31, 6391 (1990). (e) K. Miura, Y. Takeyama, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 64, 1542 (1991). (f) J. Sugimoto, K. Miura, K. Oshima, and K. Utimoto, Chem. Lett., 1991, 1319. (g) K. Miura, J. Sugimoto, K. Oshima, and K. Utimoto, Bull. Chem. Soc. Jpn., 65, 1513. (h) S. Tanaka, T. Nakamura, H. Yorimitsu, H. Shinokubo, and K. Oshima, Org. Lett., 2, 1911 (2000). (i) T. Nakamura, S. Tanaka, H. Yorimitsu, H. Shinokubo, and K. Oshima, Computes Rendus Acad. Sci. Paris, Chim., 4, 461 (2001).
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