Synthesis of functionalized allylsilanes using 3-(stannyl)-2-(silylmethyl)propene

Synthetic Communications

Volumn 27, Issue 7, 1997, Pages 1173-1181

  Kang, Kyung Tae ^a   Sung, Tae Myung ^a   Kim, Jun Keun ^a   Kwon, Yong Mok ^a  

^a Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; SILANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030902566     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708003354     Document Type: Article

References (10)

1. Kang, K. -T.; Kim, S. S.; Lee, J. C. Tetrahedron Lett. 1991, 32, 4341.
2. Kang, K. -T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495.
3. Kang, K. -T.; U, J. S.; Park, D. K.; Kim, J. K.; Kim, W. J.; Bull. Korean Chem. Soc. 1995, 16, 464.
4. The intermediacy of 3-(trifluorostannyl)-2-(trimethylsilylmethyl)propene was reported in the reaction of 2-(iodomethyl)-3-(trimethylsilyl)propene with stannous fluoride. Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877.
5. The quantitative determination of the nucleophilicity of allylsilane and allylstanne has been accomplished. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
6. Allylstannanes normally couple with acid chlorides in the presence of palladium catalyst or Lewis acid. Pereyre, M.; Quintard, J. -P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
7. Such an activation was observed in 3-stannyl-2-(stannylmethyl)propene having two allylic stannyl substituent. (a) Sano, H.; Okawara, M.; Ueno, Y. Synthesis, 1984, 933. (b) Keck, G. E.; Polani, A. Tetrahedron Lett. 1993, 34, 3223, and references therein.
8. Such an activation was observed in 3-stannyl-2-(stannylmethyl)propene having two allylic stannyl substituent. (a) Sano, H.; Okawara, M.; Ueno, Y. Synthesis, 1984, 933. (b) Keck, G. E.; Polani, A. Tetrahedron Lett. 1993, 34, 3223, and references therein.
9. Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.
10. Ochiai, M. J. Fujita, E.; Arimoto, M.; Yamaguchi, H. J. Chem. Soc. Chem. Commun. 1982, 1108.