Synthesis of cyclic sulfides by intramolecular ring opening of epoxides by thiolates generated by nickel complex catalyzed electroreduction of thioacetates

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2621-2624

  Ozaki, Shigeko ^a   Matsui, Eiki ^a   Yoshinaga, Hideaki ^a   Kitagawa, Satomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Cyclization; Electroreduction; Intramolecular epoxide opening; Nickel complex; Sulfur nucleophile

Indexed keywords

CYCLIC SULFIDE; EPOXIDE; NICKEL COMPLEX; THIOACETIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0034620937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00231-8     Document Type: Article

References (15)

1. (a) Mukerjee, A. K.; Singh, A. K. Synthesis 1975, 547-589;
2. (b) Shibasaki, M.; Ikegami, S. Tetrahedron Lett. 1977, 18, 4037-4040;
3. (c) Nicolaou, K. C.; Barnette, W. E.; Magolda, R. L. J. Am. Chem. Soc. 1981, 103, 3472-3480;
4. (d) Bach, T.; Kather, K.; Kramer, O. J. Org. Chem. 1998, 63, 1910-1918.
5. The articles published prior to 1987 have been reviewed in: (a) Vedejs, E.; Krafft; G. A. Tetrahedron 1982, 38, 2857-2881;
6. (b) Karaulova, E. N. Russian Chemical Reviews 1987, 56, 546-563.
7. (a) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330-5334;
8. (b) ibidem. 111, 5335-5340;
9. (c) Itoh, A.; Hirose, Y.; Kashiwagi, H.; Masaki, Y. Heterocycles 1994, 38, 2165-2169;
10. (d)Bach, T.; Kather, K.; Kramer, O. J. Org. Chem. 1998, 63, 1910-1918.
11. Fuzier, M.; Merrer, Y. L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6443-6446.
12. Ozaki, S.; Mastui, E.; Saiki, T.; Yoshinaga, H.; Ohmori, H. Tetrahedron Lett. 1998, 39, 8121-8124.
13. The cyclic voltammeric behavior of Ni(II)(bae) in the presence of 1a and epoxycyclohexane suggested that this complex would transfer an electron to 1a but not to the latter. (a) Stolzenberg, A. M.; Stershic, M. T. J. Am. Chem. Soc. 1988, 110, 5397-5403;
14. (b) Ozaki, S.; Mastushita, H.; Ohmori, H. J. Chem. Soc., Perkin Trans. 1 1993, 649-651.
15. Ozaki, S.; Urano, Y.; Ohmori, H. Electrochim. Acta 1997, 42, 2153-2158 and Ref. 5.