Hydrosilylation of acetylenes with catalytic biscobalthexacarbonyl complex and its application to heteroconjugate addition methodology

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6927-6932

  Isobe, Minoru ^a   Nishizawa, Rena ^a   Nishikawa, Toshio ^a   Yoza, Kenji ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b Bruker Japan Co Ltd ^*  (Japan)

Author keywords

Acetylene biscobalthexacarbonyl; Diastereoselectivity; Heteroconjugate addition; Hydrosilylation

Indexed keywords

ACETYLENE; ALKENE; BENZENE DERIVATIVE; COBALT COMPLEX; SILANE DERIVATIVE; SULFIDE; SULFONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033578597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01228-9     Document Type: Article

References (21)

1. (a) Greenfield, H.; Sternberg, H. W.; Friedel, R. A.; Wotiz, J.; Markby, R.; Wender, I. J. Am. Chem. Soc. 1956, 78, 120-124.
2. (b) Hoffman, D. M.; Hoffmann, R.; Fisel, C. R. J. Am. Chem. Soc. 1982, 104, 3858-3875.
3. (c) Kajtar, M.; Kajtar-Miklos, J.; Giacomelli, G.; Gaal, G.; Varadi, G.; Horvath, I. T.; Zucchi, C.; Palti, G. Tetrahedron: Asymmetry 1995, 6, 2177-2194.
4. (a) Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 3475-3478.
5. (b) Seyferth, D.; Nestle, M. O.; Wehman, A. T. J. Am. Chem. Soc. 1975, 97, 7417-7426.
6. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214, and references cited therein.
7. (b) Muehldorf, A. V.; Guzman-Perez, A.; Kluge, A. F. Tetrahedron Lett. 1994, 35, 8755-8758.
8. (c) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749-5759.
9. Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609-2612.
10. 6 reagent was strongly acidic and was neutralized by triethylamine and used as a solution in 2-propanol, ca. 1 M.
11. Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641-7644.
12. For isomerization of sugar acetylenes via a cobalthexacarbonyl complex, see: (a) Tanaka, S.; Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1993, 34, 5757-5760.
13. (b) Tanaka, S.; Isobe, M. Tetrahedron 1994, 50, 5633-5644.
14. (c) Jiang, Y.; Isobe, M. Tetrahedron 1996, 52, 2877-2892.
15. (d) Jiang, Y.; Ichikawa, Y.; Isobe, M. Tetrahedron 1997, 53, 5103-5122.
16. (a) Isobe, M.; Funabashi, Y.; Ichikawa, Y.; Mio, S.; Goto, T. Tetrahedron Lett. 1984, 25, 2021-2024.
17. (b) Isobe, M.; Ichikawa, Y.; Funabashi, Y.; Mio, S.; Goto, T. Tetrahedron 1986, 42, 2863-2872.
18. (a) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1980, 21, 4727-4730.
19. (b) Herunsalee, A.; Isobe, M.; Fukuda, Y.; Goto, T. Synlett 1990, 701-703.
20. (c) Herunsalee, A.; Isobe, M.; Goto, T. Tetrahedron 1991, 47, 3727-3736.
21. (d) Isobe, M.; Jiang, Y.-M. Tetrahedron Lett. 1995, 36, 567-570.