Unusual influence of substituents on ring-opening metathesis reactions

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4275-4277

  Wright, Dennis L ^a   Usher, Lynn C ^a   Estrella Jimenez, Maria ^a  

^a University of Florida   (United States)

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[No Author keywords available]

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ARTICLE;

EID: 0001461838     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016936+     Document Type: Article

References (21)

1. For reviews on olefin metathesis, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Wright, D. L. Current Org. Chem. 1999, 3, 211. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
2. For reviews on olefin metathesis, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Wright, D. L. Current Org. Chem. 1999, 3, 211. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
3. For reviews on olefin metathesis, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. Wright, D. L. Current Org. Chem. 1999, 3, 211. Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
4. For examples, see: Tallarico, J.; Randall, M. L.; Snapper, M. L. Tetrahedron 1997, 53, 16511. Tallarico, J.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997 119, 7157.
5. For examples, see: Tallarico, J.; Randall, M. L.; Snapper, M. L. Tetrahedron 1997, 53, 16511. Tallarico, J.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997 119, 7157.
6. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
7. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
8. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
9. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
10. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
11. For excellent reviews, see: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1. Noyori, R.; Hayakawa, Y. Tetrahedron 1985, 41, 5879; Mann, J. Tetrahedron 1986, 42, 4611. Rigby, J. H.; Pigge, F. C. In Organic Reactions; Paquette, L. A., Ed.; Wiley and Sons: New York, 1997; Vol. 51, p 351. Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
12. For some alternative openings, see: Dunkel, R.; Mentzel, M.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 14929. Wolkers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 53, 1905.
13. For some alternative openings, see: Dunkel, R.; Mentzel, M.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 14929. Wolkers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 53, 1905.
14. Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; Fehlhaber, H. W. Tetrahedron Lett. 1977, 18, 1669.
15. Kashman, Y.; Groweiss, A.; Shueli, J. Tetrahedron Lett. 1980, 21, 3629.
16. Two examples have been reported, with p-tBu styrene (Cuny, G. D.; Cao, J.; Sidhu, A.; Hauske, J. R. Tetrahedron 1999, 55, 8169) and with ethylene (Harmata, M.; Shao, L.; Kurti, L.; Akeywardane, A. Tetrahedron Lett. 1999, 40, 1075).
17. Two examples have been reported, with p-tBu styrene (Cuny, G. D.; Cao, J.; Sidhu, A.; Hauske, J. R. Tetrahedron 1999, 55, 8169) and with ethylene (Harmata, M.; Shao, L.; Kurti, L.; Akeywardane, A. Tetrahedron Lett. 1999, 40, 1075).
18. Fohlisch, B.; Gehrlach, E.; Geywitz, B. Chem. Ber. 1987, 120, 1815.
19. Catalyst 3 was superior to 4 in all cases except 1-hexene, where lower yields resulted from a second cross-metathesis between 5c and 1-hexene. For catalyst 3, see: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
20. Olefin assigned by coupling constant or NOE analysis.
21. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.