Use of Silicon-Based Tethers to Control Diastereofacial Selectivity in Azomethine Ylide Cycloadditions

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 493-498

  Garner, Philip ^a   Cox, Philip B ^a   Anderson, James T ^a   Protasiewicz, John ^a   Zaniewski, Rebecca ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000615743     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609034     Document Type: Article

References (21)

1. Preliminary Communication: Garner, P. P.; Cox, P. B.; Klip-penstein, S. J.; Youngs, W. J.; McConville, D. B. J. Org. Chem. 1994, 59, 6510-6511.
2. Zaccardi, J.; Alluri, M.; Ashcroft, J.; Bernan, V.; Korshalla, J. D.; Morton, G. O.; Siegel, M.; Tsao, R.; Williams, D. R.; Maiese, W.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4045-4047. This paper suggests that the previously proposed structure for naphthyridinomycin is actually an artifact of the fermentation procedure and that the naturally occurring form of naphthyridinomycin is actually bioxalomycin β2. If this is true, then the related SF-1739 may also possess a bis-oxazolidine structure.
3. Gould, S. J.; He, W.; Cone, M. C. J. Nat. Prod. 1993, 56, 1239-1245.
4. For a review of synthetic work on naphthyridinomycin and cyanocycline A, including total syntheses by the Evans and Fukuyama groups, see: Fukuyama, T. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 2, pp 189-249.
5. Garner, P.; Sunitha, K.; Ho, W.-B.; Youngs, W. J.; Kennedy, V. O.; Djebli, A. J. Org. Chem. 1989, 54, 2041-2042.
6. (a) Shea, K. J.; Zandi, K. S.; Staab, A. J.; Carr, R. Tetrahedron Lett. 1990, 31, 5885-5888.
7. (b) Craig, D.; Reader, J. C. Ibid. 1990, 31, 6585-6588.
8. (c) Gillard, J. W.; Fortin, R.; Grimm, E. L.; Maillard, M.; Tjepkema, M.; Bernstein, M. A.; Glaser, R. Ibid. 1991, 32, 1145-1148.
9. (d) Shea, K. J.; Staab, A. J.; Zandi, K. S. Ibid. 1991, 32, 2715-2718.
10. (e) Fleming, S. A.; Ward, S. C. Ibid. 1992, 33, 1013-1016.
11. (f) Craig, D.; Reader, J. C. Ibid. 1992, 33, 4073-4076.
12. (g) Stork, G.; Chan, T. Y.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579.
13. (g) Rumbo, A.; Castedo, L.; Mouriño; Mascareñas, J. L. J. Org. Chem. 1993, 58, 5585-5586.
14. (h) Crimmins, M. T.; Guise, L. E. Tetrahedron Lett. 1994, 35, 1657-1660.
15. (i) For a recent review of this area, see: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1257.
16. Cf. Agyin, J. K.; Morrison, H.; Siemiarczuk, A. J. Am. Chem. Soc. 1995, 117, 3875-3876.
17. Ho, W. B. The Asymmetric Synthesis of (-)-Quinocarcin. Ph.D. Dissertation, Case Western Reserve University, Cleveland, OH 1992.
18. Support for this hypothesis initially came fron a TS modeling study which indicated a crossover from endo-re to endo-si selectivity as a function of tether structure. See reference 1 for details.
19. Cf. Markiewicz, W. T.; Padyukova, N. Sh.; Samek, S.; Smrt, J. Collect. Czech. Chem. Commun. 1980, 45, 1860-1865.
20. The authors have deposited the atomic coordinates and thermal parameters for compound 24a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
21. The connection between TS ring size and stereocontrol in these intramolecular dipolar cycloaddition reactions is reminiscient of, and possibly related to, Still's seminal work on conformationally mediated stereocontrol in macrocyclic systems. Cf. Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996.