A new method for cross-metathesis of terminal olefins

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7427-7430

  O'Leary, Daniel J ^a,b   Blackwell, Helen E ^a   Washenfelder, Rebecca A ^a,b   Grubbs, Robert H ^a  

^a California Institute of Technology ^*  (United States)

^b POMONA COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DIMERIZATION; ISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01647-5     Document Type: Article

References (20)

1. 2. For a recent review, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
2. 3. Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
3. 4. Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162-5163.
4. 5. Crowe, W. E.; Goldberg, D. R.; Zhang, Z. J. Tetrahedron Lett. 1996, 37, 2117-2120.
5. 6. Brummer, O.; Ruckert, A.; Blechert, S. Chem. Eur. J. 1997, 3, 441-446.
6. 7. Gibson, S. E.; Gibson, V. C.; Keen, S. P. Chem. Commun. 1997, 1107-1108.
7. 8. Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem., Intl. Ed. Engl. 1997, 36, 2518-2520.
8. 9. Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
9. 10. Scheider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Intl. Ed. Engl. 1997, 36, 257-259.
10. 11. For a recent report from these laboratories, see: Hillmyer, M. A.; Nguyen, S. T.; Grubbs, R. H. Macromolecules 1997, 30, 718-721, and references cited therein.
11. 12. Used as delivered from TCI America.
12. 2 (5 ml) and the disubstituted olefin (1.0 mmol, 2 equiv) are added in succession. The terminal olefin (0.5 mmol, 1 equiv) is added and the septum is quickly replaced with a condenser which is connected to a nitrogen bubbler. The flask is immersed in an oil bath and refluxed (bath temperature: 45 °C) for a period of 12 hr or until the reaction is judged complete by TLC.
13. 4Ru=CHR). See: Schwab, P. E.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110, and Ullman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.
14. 4Ru=CHR). See: Schwab, P. E.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110, and Ullman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.
15. 15. In contrast, the use of neat allyl acetate provided only marginal amounts of the desired cross-product, presumably due to the statistically favored solvent dimerization which dominates the catalytic cycle.
16. 16. A similar two-step procedure has been implemented for telechelic polymer syntheses. See Ref. 11 and: Nubel, P. O.; Yokelson, H. B.; Lutman, C. A.; Bouslog, W. G.; Behrends, R. T.; Runge, K. D. J. Mol. Catal. A: Chem. 1997, 115, 43-50.
17. 17. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
18. 18. Amino acid derivative 6 was prepared according to a modified literature procedure. See: Sugano, H.; Miyoshi, M. J. Org. Chem. 1976, 41, 2352-2353.
19. 19. For a recent application of a metathesis homodimerization strategy, see: Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106-5109.
20. 20. O'Leary, D. J.; Blackwell, H. E.; Washenfelder, R. A.; Van Nostrand, M.; Porco, Jr., J. A.; Grubbs, R. H. Manuscript in preparation.