γ-Regioselective reaction of metaloxysilyl-substituted allyllithium derived from allyldiphenylsilanol

Tetrahedron Letters

Volumn 38, Issue 29, 1997, Pages 5189-5192

  Takaku, Koji ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; ORGANOSILICON DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030849981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01124-6     Document Type: Article

References (21)

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2. Panek, J. S. In Comprehensive Organic Synthesis ; Trost, B. M., Fleming, I., Schreiber, S. L. Eds; Pergamon Press: Oxford, 1991; Vol. 1 Chapter 2.5 pp 579-627. Colvin, E. W. Silicon Reagents in Organic Synthesis, Butterworths and Co Ltd.: London, 1981. Colvin, E. W. Silicon Reagents in Organic Synthesis, Academic Press: London, 1988.
3. Panek, J. S. In Comprehensive Organic Synthesis ; Trost, B. M., Fleming, I., Schreiber, S. L. Eds; Pergamon Press: Oxford, 1991; Vol. 1 Chapter 2.5 pp 579-627. Colvin, E. W. Silicon Reagents in Organic Synthesis, Butterworths and Co Ltd.: London, 1981. Colvin, E. W. Silicon Reagents in Organic Synthesis, Academic Press: London, 1988.
4. Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics. 1983, 2, 1694-1696. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Org. Synth. 1993, Col. Vol. 8, 315-321.
5. Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics. 1983, 2, 1694-1696. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Org. Synth. 1993, Col. Vol. 8, 315-321.
6. Fleming, I. Chemtracts. Org. Chem. 1996, 9, 1-64. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics. 1983, 2, 1694-1696. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Org. Synth. 1993, Col. Vol. 8, 315-321.
7. The reaction of allyl(diethylamino)dimethylsilane with butyllithium has been reported to provide silyl-substituted allyllithium without contamination by the substitution products. Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957-958. Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007.
8. The reaction of allyl(diethylamino)dimethylsilane with butyllithium has been reported to provide silyl-substituted allyllithium without contamination by the substitution products. Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957-958. Tamao, K.; Nakajo, E.; Ito, Y. Tetrahedron 1988, 44, 3997-4007.
9. Allyldiphenylsilanol was easily prepared in 62% yield by treatment of hexaphenyltrisiloxane with allylmagnesium chloride under reflux in ether. Sieburth, S. M.; Mu, W. J. Org. Chem. 1993, 58, 7584-7586. Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464.
10. Allyldiphenylsilanol was easily prepared in 62% yield by treatment of hexaphenyltrisiloxane with allylmagnesium chloride under reflux in ether. Sieburth, S. M.; Mu, W. J. Org. Chem. 1993, 58, 7584-7586. Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464.
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17. 8 formula presented
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21. 2Si: C, 76.26; H, 6.40.