Silicon-tethered 1,3-dipolar cycloaddition of 4-hydroxy-2-isoxazoline 2-oxides

Journal of the American Chemical Society

Volumn 118, Issue 39, 1996, Pages 9446-9447

  Righi, Paolo ^a   Marotta, Emanuela ^a   Landuzzi, Andrea ^a   Rosini, Goffredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOXAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029946467     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961816w     Document Type: Article

References (21)

1. Rosini, G. The Henry (Nitroaldol) Reaction. In Comprehensive Organic Synthesis; Trost, B. M.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 321.
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3. Rosini, G.; Marotta, E.; Righi, P.; Seerden, J.-P. J. Org. Chem. 1991, 56, 6258-6260.
4. Review: Wade, P. A. Intramolecular 1,3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 1111-1168 and references therein cited.
5. Review on silicon-tethered reactions: Bols, M.; Skydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
6. Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248. Stork, G.; Chan, T. Y.; Breault G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as a temporary tether: Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
7. Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248. Stork, G.; Chan, T. Y.; Breault G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as a temporary tether: Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
8. Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248. Stork, G.; Chan, T. Y.; Breault G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as a temporary tether: Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
9. Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248. Stork, G.; Chan, T. Y.; Breault G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as a temporary tether: Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
10. Stork, G.; La Clair, J. J. J. Am. Chem. Soc. 1996, 118, 247-248. Stork, G.; Chan, T. Y.; Breault G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7056. It has been recently reported that also magnesium or aluminum can serve as a temporary tether: Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
11. (a) Tamao, K.; Nakagawa, Y.; Ito, Y. Org. Synth. 1995, 73, 94-109.
12. (b) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 6478-6480.
13. Very similar results were obtained with chlorodiphenylvinylsilane.
14. The large majority of the reported silicon-tethered cycloadditons are of the Diels-Alder type: see ref 5.
15. One of the reviewers pointed out that an earlier example of silicon-tethered 1,3-dipolar cycloaddition was presented by G. Stork at the 32nd National Organic Symposium held in 1991 in Minneapolis (Roger Adams Award lecture, Book of Abstracts, pp 120-121).
16. 13C NMR spectra. The "all-cis-fused" stereochemistry of the tricyclic system was confirmed by NOE experiments: saturation of the C(7)H signal gave a ca. 2% enhancement of the C(1)H signal.
17. It is possible to observe by TLC the formation of a transient species which smoothly interconverts to the tricyclic product.
18. Brook, M. A.; Seebach, D. Can. J. Chem. 1987, 65, 836-850. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-166 and references cited therein.
19. Brook, M. A.; Seebach, D. Can. J. Chem. 1987, 65, 836-850. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137-166 and references cited therein.
20. Tamao, K.; Yamauki, Y.; Ito, Y. Chem. Lett. 1987, 171-174. See also ref 7a and references cited therein.
21. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Org. Synth. 1990, 69, 96-105.