Ring opening cross-metathesis on solid support

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5237-5240

  Cuny, Gregory D ^a   Cao, Jingrong ^a   Hauske, James R ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; STYRENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; SYNTHESIS; TECHNIQUE;

EID: 0030857041     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01144-1     Document Type: Article

References (19)

1. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446 and references therein.
2. (a) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610.
3. (b) Schneider, M. F.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 411.
4. (a) Snapper, M. L.; Tallarico, J. A.; Randell, M. L. J. Am. Chem. Soc. 1997, 119, 1478.
5. (b) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew Chem. Int. Ed. Engl. 1997, 36, 257.
6. Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1979.
7. (a) Ellman, J. A. Acc. Chem. Res. 1996, 29, 132.
8. (b) a 5000-membered library has been prepared utilizing the methodoloy described herein and will be reported in a separate publication.
9. Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998.
10. Noels, A. F.; Demonceau, A.; Carlier, E.; Hubert A. J.; Márquez-Silva, R.-L.; Sánchez-Delgado, R. A. J. Chem. Soc., Chem. Commun. 1988, 783.
11. (a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
12. (b) Schwab, P.; France M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
13. 1H NMR or by HPLC analysis of the corresponding BOC-derivatives.
14. Hauske, J. R.; Dorff, P. Tetrahedron Lett. 1995, 36, 1589.
15. Coste, J.; Dufour, M.-N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 31, 669.
16. Relative stereochemistry at the benzylic position was tentatively assigned based on MM3 calculations that predicted 16a to be 2.7 kcal/mol lower in energy compared to its epimer.
17. Ukhov, S. V.; Konshin, M. E. Khim. Geterosikl. Soedin. 1992, 28, 92.
18. For an example of augmented diastereoselectivity on the solid-phase see: Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998.
19. Calculated yields were based on resin loading and recovery of crude product cleaved directly from the resin. The purity of the material (> 85%) was based on HPLC analysis.