Synthesis of highly enantio-enriched allylsilanes via palladium-catalyzed intramolecular bis-silylation. Determination of the enantiomeric excesses through regio- and stereoselective hydroboration with 9-BBN

Tetrahedron Asymmetry

Volumn 8, Issue 6, 1997, Pages 859-862

  Suginome, Michinori ^a   Iwanami, Taisuke ^a   Matsumoto, Akira ^a   Yoshihiko, Ito ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0030897604     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00073-6     Document Type: Article

References (25)

1. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1326.
2. Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963-4965. Hayashi, T.; Konishi, M.; Kumada, M. J. Org. Chem. 1983, 48, 281-282.
3. Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963-4965. Hayashi, T.; Konishi, M.; Kumada, M. J. Org. Chem. 1983, 48, 281-282.
4. (a) Hayashi, T; Konishi, M.; Ito, H.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4962-4963.
5. (b) Mikami, K.; Maeda, T.; Kishi, N.; Nakai, T. Tetrahedron Lett. 1984, 25, 5151-5154.
6. (c) Hayashi, T.; Konishi, M.; Okamoto, Y.; Kabeta, K.; Kumada, M. J. Org. Chem. 1986, 51, 3772-3781.
7. (d) Fleming, I.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1986, 1456-1457.
8. (e) Sparks, M. A.; Panek, J. S. J. Org. Chem. 1991, 56, 3431-3438.
9. (f) Fleming, I.; Higgins, D.; Lawrence, N. J.; Thomas, A. P. J. Chem. Soc., Perkin Trans. 1 1992, 3331-3349.
10. (g) Buckle, M. J. C.; Fleming, I.; Gil, S. Tetrahedron Lett. 1992, 33, 4479-4482.
11. (h) Bhushan, V.; Lohray, B. B.; Enders, D. Tetrahedron Lett. 1993, 34, 5067-5070.
12. Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061-3062.
13. a) Murakami, M.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987-3988.
14. b) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498.
15. c) Suginome, M.; Matsumoto, A.; Nagata, K.; Ito, Y. J. Organomet. Chem. 1995, 499, C1-C3.
16. Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608-9609.
17. All HPLC analyses of the alcohols 6 and 7 were carried out for their N-(3,5-dinitrophenyl)carbamate derivatives with a SUMICHIRAL OA-4500 column (hexane/dichloroethane/ethanol=50:15:1).
18. 2K as a diimide source resulted in no reaction. Pasto, D. J.; Taylor, R. T. In Organic Reactions, Vol. 40, Paquette, L. A. Ed., Wiley, 1991, pp 91-155.
19. . Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
20. . Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
21. In sharp contrast to our observation, a similar method involving hydrogenation using a Pd/C catalyst was successfully employed for e.e. determination of 1-(dimethylphenylsilyl)-1-phenyl-2-butene. Fleming, I.; Higgins, D.; Lawrence, N. J.; Thomas, A. P. J. Chem. Soc., Perkin Trans, 1 1992, 3331-3349.
22. Murakami, M.; Oike, H.; Sugawara, M.; Suginome, M.; Ito, Y. Tetrahedron 1993, 49, 3933-3946.
23. Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1984, 49, 4224-4226. Fleming, I.; Sarkar, A. K.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1987, 157-159.
24. Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1984, 49, 4224-4226. Fleming, I.; Sarkar, A. K.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1987, 157-159.
25. Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1992, 3309-3326.