Reductive desulfurization using the Raney nickel - Sodium hypophosphite combination system without racemization of a secondary alcohol

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2271-2274

  Nishide, Kiyoharu ^a   Shigeta, Yukihiro ^a   Obata, Kenichi ^a   Inoue, Takehisa ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; CHIRALITY; DESULFURIZATION; DRUG SYNTHESIS; REDUCTION; TECHNIQUE;

EID: 0030009687     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00273-0     Document Type: Article

References (22)

1. a) Pizey, J. S. Synthetic Reagents, Vol. 2, chapter 4, John Wiley & Sons Inc., New York, 1974.
2. b) Boekelheide, V.; Anderson, P. H.; Hylton, T. A. J. Am. Chem. Soc. 1974, 96, 1558-1564.
3. c) Kondo. K.; Negishi, A.; Matsui, K.; Tunemoto, D.; Masamune, S. J. Chem. Soc., Chem. Commun. 1972, 1311-1312.
4. d) Tsuchihashi, G.; Mitamura, S.; Ogura, K. Tetrahedron Lett. 1976, 855-858.
5. e) Solladié, G.; Greck, C.; Demailly, G.; Solladié-Cavallo, A. Tetrahedron Lett. 1982, 23, 5047-5050.
6. Caubère, P.; Coutrot, P. 'Reduction of Sulfur-Carbon Bonds and of Other Heteroatoms Bonded to Tetrahedral Carbon' in "Comprehensive Organic Synthesis", Vol. 8, p 835-870, Ed. by Trost, B. M.; Fleming, I., Pergamon Press, Oxford, 1991.
7. Mozingo, R. Organic Syntheses, Coll. Vol. III 1955, 181-183.
8. Epimerization: a) Peppiatt, E. G.; Wicker, R. J. J. Chem. Soc. 1955, 3122-3125.
9. b) Eliel, E. L.; Schroeter, S. H. J. Am. Chem. Soc. 1965, 87, 5031-5038.
10. c) Ishibashi, H.; Sato, K.; Ikeda, M.; Maeda, H.; Akai, S.; Tamura, Y. J. Chem. Soc., Perkin Trans. I 1985, 605-609.
11. d) Ishibashi, H.; So, T. S.; Okochi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M. J. Org. Chem. 1991, 56, 95-102.
12. Bonner, W. A. J. Am. Chem. Soc. 1952, 74, 1033-1034.
13. Nakamura, K.; Ushio, K.; Oka, S.; Ohno, A.; Yasui, S. Tetrahedron Lett. 1984, 25, 3979-3982.
14. a) Billek, G.; Kindl, H.; Schimpl, A.; Schmook, F. P. J. Label. Compounds 1969, 5, 3-7.
15. b) Montgomery, J. A.; Hewson, K.; Laseter, A. G. Carbohyd. Res. 1973, 27, 303-308.
16. c) Passannanti, S.; Paternostro, M. P.; Piozzi, F.; Savona, G. J. Heterocyclic Chem. 1977, 14, 103-106.
17. Monti, D.; Gramatica, P.; Speranza, G.; Manitto, P. Tetrahedron Lett. 1983, 24, 417-418.
18. Optically active arylthio- and benzylthioalcohols were prepared from (R)-styrene oxide or (R)-epoxyoctane with lithium thiolate in tetrahydrofuran in high yields.
19. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
20. Debenzylation with Raney nickel: Greene, T. W.; Wuts, P. G. M. "Protective Groups in Organic Synthesis, 2nd ed.," John Wiley & Sons, Inc., 1991, New York. Also see ref. 4c and 4d.
21. a) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021-3028.
22. b) Oikawa, Y.; Tanaka, T.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1984, 25, 5397-5400.