Organothio groups as electroauxiliaries: electrooxidative inter-and intramolecular carbon-carbon bond formation

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3157-3160

  Yoshida, Jun Ichi ^a   Sugawara, Masanobu ^a   Kise, Naoki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG ACTIVATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0029983136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00516-3     Document Type: Article

References (24)

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5. Yoshida J.; Isoe, S. Tetrahedron Lett., 1987, 28, 6621-6624; Suda, K.; Hotoda, K.; Watanabe, J.; Shiozawa, K.; Takanami, T. J. Chem. Soc., Perkin Trans. 1., 1992, 1283-1284; Yoshida, J.; Ishichi, Y.; Nishiwaki, K.; Shiozawa, S.; Isoe, S. Tetrahedron Lett., 1992, 33, 2599-2602.
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7. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
8. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
9. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
10. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
11. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
12. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
13. Uneyama, K.; Torii, S. Tetrahedron Lett., 1971, 4, 329-332; Mandai, T.; Irei, H.; Kawada, M.; Otera, J. Tetrahedron Lett., 1984, 25, 2371-2374; Mandai, T.; Yasunaga, H.; Kawada, M.; Otera, J. Chem. Lett., 1984, 715-716; Yoshida, J.; Isoe, S. Chem. Lett., 1987, 631-634; Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718-719; Balavoine, G.; Gref, A.; Fischer, J.-C.; Lubineau, A. Tetrahedron Lett. 1990, 31, 5761-5764; Kimura, M.; Yamamoto, Y.; Sawaki, Y. Denki Kagaku, 1993, 61, 862; Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc., 1994, 116, 2653-2654, and references cited therein.
14. Recently electrooxidative intramolecular coupling between benzylsulfides and aromatic rings has been reported. Kimura, M.; Ono, T.; Hayakawa, T.; Sawaki, Y. The Abstract of 18th Symposium of Electroorganic Chemistry, 1995, ppl-2.
15. A similar transformation has been achieved by using triorganotin as an electroauxiliary. See: Yoshida, J.; Itoh, M.; Isoe, S. J. Chem. Soc., Chem. Commun., 1993, 547-549.
16. Nishiyama, H.; Narimatsu, S.; Sakuta, K.; Itoh, K. J. Chem. Soc., Chem. Commun., 1982, 459-460. Lewis acid promoted reactions of (O,Se) acetals with carbon nucleophiles, see also: Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147 and references cited therein.
17. Nishiyama, H.; Narimatsu, S.; Sakuta, K.; Itoh, K. J. Chem. Soc., Chem. Commun., 1982, 459-460. Lewis acid promoted reactions of (O,Se) acetals with carbon nucleophiles, see also: Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147 and references cited therein.
18. A similar transformation has been achieved by using triorganotin as an electroauxiliary. See: Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc., 1992, 114, 7594-7595.
19. Nokami, J.; Hatte, M.; Wakabayashi, S.; Okawara, R. Tetrahedron Lett. 1980, 21, 2557-2558.
20. Nokami, J.; Ryokume, K.; Inada, J. Tetrahedron Lett., 1995, 36, 6099-6100.
21. Suzuki, K.; Inanaga, J.; Yamaguchi, M. Chem. Lett., 1979, 1227-1228; Corey, M. G. Bock, M. G. Tetrahedron Lett., 1975, 3269-3270.
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23. Lithiation of S,O-acetals: For example, Otera, J.; Niibo, Y.; Nozaki, H. J. Org. Chem., 1989, 54, 5003-5007; Sato, T.; Okura, S.; Otera, J.; Nozaki, H. Tetrahedron Lett., 1987, 28, 6299-6302.
24. Lithiation of S,O-acetals: For example, Otera, J.; Niibo, Y.; Nozaki, H. J. Org. Chem., 1989, 54, 5003-5007; Sato, T.; Okura, S.; Otera, J.; Nozaki, H. Tetrahedron Lett., 1987, 28, 6299-6302.