Synthesis of cyclopropylsilanols by the Simmons-Smith reaction of alkenylsilanols and lithium alkenylsilanolates

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 461-464

  Hirabayashi, Kazunori ^a   Mori, Atsunori ^a   Hiyama, Tamejiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031023977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02326-X     Document Type: Article

References (20)

1. Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett., 1996, 517-518; Mori, A.; Hishida, T.; Soga, Y.; Kawakami, Y. Chem. Lett., 1995, 107-108. See also: Sieburth, S. M.; Fensterbank, L. J. Org. Chem., 1993, 58, 6314-6318; Sieburth, S. M.; Mu, W. J. Org. Chem, 1993, 58, 7584-7586.
2. Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett., 1996, 517-518; Mori, A.; Hishida, T.; Soga, Y.; Kawakami, Y. Chem. Lett., 1995, 107-108. See also: Sieburth, S. M.; Fensterbank, L. J. Org. Chem., 1993, 58, 6314-6318; Sieburth, S. M.; Mu, W. J. Org. Chem, 1993, 58, 7584-7586.
3. Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett., 1996, 517-518; Mori, A.; Hishida, T.; Soga, Y.; Kawakami, Y. Chem. Lett., 1995, 107-108. See also: Sieburth, S. M.; Fensterbank, L. J. Org. Chem., 1993, 58, 6314-6318; Sieburth, S. M.; Mu, W. J. Org. Chem, 1993, 58, 7584-7586.
4. Mori, A.; Sato, H.; Mizuno, K.; Hiyama, T.; Shintani, K.; Kawakami, Y. Chem. Lett., 1996, 517-518; Mori, A.; Hishida, T.; Soga, Y.; Kawakami, Y. Chem. Lett., 1995, 107-108. See also: Sieburth, S. M.; Fensterbank, L. J. Org. Chem., 1993, 58, 6314-6318; Sieburth, S. M.; Mu, W. J. Org. Chem, 1993, 58, 7584-7586.
5. Ajima, K.; Nomura, M.; Mori, A.; Kawakami, Y. Polym. Prepr., Jpn., 1995, 44, 3011; Kawakami, Y.; Sugisaka, T. J. Memb. Sci., 1990, 50, 189-205; Kawakami, Y.; Toida, K. Macromolecules, 1995, 28, 816-826 and references therein.
6. Ajima, K.; Nomura, M.; Mori, A.; Kawakami, Y. Polym. Prepr., Jpn., 1995, 44, 3011; Kawakami, Y.; Sugisaka, T. J. Memb. Sci., 1990, 50, 189-205; Kawakami, Y.; Toida, K. Macromolecules, 1995, 28, 816-826 and references therein.
7. Ajima, K.; Nomura, M.; Mori, A.; Kawakami, Y. Polym. Prepr., Jpn., 1995, 44, 3011; Kawakami, Y.; Sugisaka, T. J. Memb. Sci., 1990, 50, 189-205; Kawakami, Y.; Toida, K. Macromolecules, 1995, 28, 816-826 and references therein.
8. Silanols are generally prepared by careful hydrolysis of the corresponding chlorosilanes but readily converted via condensation to disiloxane. Therefore, silanols with a bulky substituent, relatively easy to prepare, have rarely been used in organic synthesis. Recent synthetic effort using silanols: Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett., 1996, 37, 6781-6784.
9. Epoxidation of alkenylsilanols: Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun., 1988, 1280-1281; Chan, T. H.; Chen. L. M.; Wang, D.; Li, L. H. Can. J. Chem., 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun., 1993, 436-437.
10. Epoxidation of alkenylsilanols: Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun., 1988, 1280-1281; Chan, T. H.; Chen. L. M.; Wang, D.; Li, L. H. Can. J. Chem., 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun., 1993, 436-437.
11. Epoxidation of alkenylsilanols: Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun., 1988, 1280-1281; Chan, T. H.; Chen. L. M.; Wang, D.; Li, L. H. Can. J. Chem., 1993, 71, 60-67; Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun., 1993, 436-437.
12. (a) Simmons, H. E.; Cairns, T. L.; Vladuchick, S. A.; Hoiness, C. M. Org. React. 1973, 20, 1-131;
13. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron, 1968, 24, 53-58;
14. (c)Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc., 1992, 114, 2592-2602;
15. (d)Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett., 1992, 33, 2575-2578;
16. (e) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett., 1992, 61-64.
17. 2 is reported to proceed at higher temperatures. See ref 5a.
18. Charette, A. B.; Brochu, C. J. Am. Chem. Soc. 1995, 117, 11367-11368.
19. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics, 1983, 2, 1694-1696.
20. So far, attempts at protodesilylation with some fluoride reagents have been unsuccessful.