Ligand-controlled, complementary stereoselectivity in the platinum-catalyzed intramolecular silaboration of alkenes

Journal of the American Chemical Society

Volumn 128, Issue 41, 2006, Pages 13366-13367

  Ohmura, Toshimichi ^a   Furukawa, Hideki ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; LIGAND; PLATINUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SILABORATION; STEREOCHEMISTRY;

EID: 33750053862     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065588+     Document Type: Article

References (21)

1. (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
2. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813.
3. (c) Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289.
4. (a) Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090.
5. (b) Tamao, K.; Nakagawa, Y.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 3712.
6. (a) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487.
7. (b) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608.
8. (a) Leighton, J. L.; Chapman, E. J. Am. Chem. Soc. 1997, 119, 12416.
9. (b) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. Tetrahedron 2003, 59, 8889.
10. Curtis, N. R.; Holmes, A. B. Tetrahedron Lett. 1992, 33, 675.
11. Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
12. For recent reviews on bismetalation. see (a) Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320.
13. (b) Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221.
14. (a) Suginome, M.; Ito, Y. J. Organomet. Chem. 2003, 680, 43.
15. For recent examples, see (b) Suginome, M.; Ohmura, T.; Miyake, Y.; Mitani, S.; Ito, Y.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 11174.
16. (c) Ohmura, T.; Suginome, M. Org. Lett. 2006, 8, 2503.
17. The substrates 1 and 3 were synthesized by the reaction of homoallylic alcohols with (chlorodiphenylsilyl)pinacolborane in the presence of pyridine. See the Supporting Information for details.
18. For a recent review on synthetic utilities of alkyl boronates, see Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695.
19. Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 15334.
20. Sadhu, K. M.; Matteson, D. S. Organometallics 1985, 4, 1687.
21. Tamao, K.; Nakagawa, Y.; Ho, Y. Org. Synth. 1994, 73, 94.