Stereoselective double ring closing metathesis reactions in the synthesis of spirocyclic compounds

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 2027-2029

  Wallace, Debra J ^a   Cowden, Cameron J ^a   Kennedy, Derek J ^a   Ashwood, Michael S ^a   Cottrell, Ian F ^a   Dolling, Ulf H ^a,b  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Ring closing metathesis; Spirocyclic; Stereoselective

Indexed keywords

AMINO ACID; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034681742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00095-2     Document Type: Article

References (18)

1. Bazan, G. C.; Oskam, J. H.; Cho, H.-N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 112, 6899 and references cited therein.
2. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; J. Am. Chem. Soc. 1992, 114, 3974
3. (b) Wu, Z.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Organomet. Chem. 1995, 497, 195.
4. © Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
5. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
6. For recent reviews of the metathesis reaction, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
7. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
8. © Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
9. (d) Tetrahedron Symposium in Print; Snapper, M. L.; Hoveyda, A. H., Eds; 1999, 55, 8141.
10. (e) Alkene Metathesis in Organic Synthesis; Furstner, A., Ed.; Top. Organomet. Chem. 1998, 1.
11. (a) Baylon, C.; Heck, M.-P.; Mioskowski, C. J. Org. Chem. 1999, 64, 3354.
12. (b) Lautens, M.; Hughes, G. Angew. Chem. Int. Ed. Engl. 1999, 38, 129.
13. © Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8628.
14. (d) Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247.
15. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333.
16. (f) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
17. Baker, R.; Curtis, N. R.; Elliott, J. M.; Harrison, T.; Hollingworth, G. J.; Jackson, P. S.; Kulagowski, J. J.; Seward, E. M.; Swain, C. J.; Williams, B. J. International Patent WO97/49710, 1997.
18. All new compounds gave satisfactory spectroscopic and HRMS data.