Stereoselective hydrogenation of α-sulfinyl radical generated from alkyl radical addition to α-(1-hydroxyethyl)vinyl sulfoxide

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5553-5556

  Mase, Nobuyuki ^a   Wake, Shutaro ^a   Watanabe, Yoshihiko ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA (1 HYDROXYETHYL)VINYLSULFOXIDE; RADICAL; SULFOXIDE; TRIBUTYLIN HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGEN BOND; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032581660     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01118-6     Document Type: Article

References (28)

1. 1. (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of radical reactions; VCH: Weinheim, 1995.
2. (b) Sinadja, W. Synlett 1994, 1.
3. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296.
4. 2. (a) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233.
5. (b) Zahouily, M.; Caron, G.; Carrupt, P.-A.; Knouzi, N.; Renaud, P. Tetrahedron Lett. 1996, 37, 8387.
6. (c) Renaud, P.; Bourquard, T. Synlett 1995, 1021.
7. (d) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547.
8. (e) Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703.
9. (f) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259.
10. (g) Mesmaeker, A. D.; Waldner, A., Hoffmann, P.; Mindt, T. Synlett 1993, 871.
11. (h) Waldner, A.; Mesmaeker, A. D.; Hoffmann, P.; Mindt, T.; Winkler, T. Synlett 1991, 101.
12. (i) Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc., Chem. Commun. 1991, 1151.
13. (j) Snider, B. B.; Wan, B. Y.-F.; Buckman, B. O.; Foxman, B. M. J. Org. Chem. 1991, 56, 328.
14. 3. (a) Mase, N.; Walanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
15. (b) Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure & Appl. Chem. 1996, 68, 711.
16. (c) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464.
17. 4. Bonfand, E.; Gosselin, P.; Maignan, C. Tetrahedron: Asymmetry 1993, 4, 1667.
18. 5. Arai, Y.; Kuwayama, S.; Takeuchi, Y.; Koizumi, T. Tetrahedron Lett. 1985, 26, 6205.
19. 6. Barker, S. A.; Brimacombe, J. S.; Harnden, M. R.; Jarvis, J. A. J. Chem. Soc. 1963, 3403.
20. 7. Commercially available ethyl iodide, isopropyl iodide, and cyclohexyl iodide were distilled before use in the presence of copper. tert-Butyl iodide was prepared by the reported procedure; see, Masada, H.; Murotani, Y. Bull. Chem. Soc. Jpn. 1980, 53, 1181.
21. 8. Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 403.
22. 1H NMR; see: Kingsbury, C. A.; Auerbach, R. A. J. Org. Chem. 1971, 36, 1737.
23. 10. Marino, J. P.; Viso, A.; Lee, J.-D. J. Org. Chem. 1997, 62, 645.
24. 11. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
25. 12. MOPAC 93, Stewart, J. J. P. J. Comp. Chem. 1989, 10, 210.
26. -1 which appeared at 0.1 mol/L was not observed at 0.01 mol/L.
27. 14. (formula presented)
28. 15. The radical intermediate having different conformation has been postulated in the reaction of β-hydroxy-α-methylene-carboxylates, where bulky alkyl radicals show low diastereoselectivity; see, Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576.