Extensive isomerization of alkenes using a bifunctional catalyst: An alkene zipper

Journal of the American Chemical Society

Volumn 129, Issue 31, 2007, Pages 9592-9593

  Grotjahn, Douglas B ^a   Larsen, Casey R ^a   Gustafson, Jeffery L ^a   Nair, Reji ^a   Sharma, Abhinandini ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; CLAISEN REARRANGEMENT; COMPLEX FORMATION; DIASTEREOISOMER; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS;

EID: 34547824474     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073457i     Document Type: Article

References (24)

1. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
2. Uma, R.; Crevisy, C.; Gree, R. Chem. Rev. 2003, 103, 27-51.
3. Kuznik, N.; Krompiec, S. Coord. Chem. Rev. 2007, 251, 222-233.
4. Herrmann, W. A.; Prinz, M. In Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 3, pp 1119-1130.
5. Negishi, E.-I. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 2, pp 2783-2788.
6. Suzuki, H.; Takao, T. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 309-331.
7. Otsuka, S.; Tani, K. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 199-209.
8. Rüba, E.; Simanko, W.; Mauthner, K.; Soldouzi, K. M.; Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1999, 18, 3843-3850.
9. Gibson, T.; Tulich, L. J. Org. Chem. 1981, 46, 1821-1823.
10. Iranpoor, N.; Mottaghinejad, E. J. Organomet. Chem. 1992, 423, 399-404.
11. In eq 1, isomerization to the enol requires a movement over n-1 positions, all of which can be reasonably attributed to catalysis by metal. The final enol-keto tautomerization may or may not involve metal catalyst but for simplicity is included in the total count of n.
12. The term "zipper" has also been applied to alkyne isomerization by superstoichiometric amounts of strong bases: Brown, C. A.; Yamashita, A. J. Am. Chem. Soc. 1975, 97, 891-892.
13. Bifunctional reactivity may be involved, but salts of simple amines also work: Abrams, S. R.; Nucciarone, D. D.; Steck, W. F. Can. J. Chem. 1983, 61, 1073-1076.
14. Slugovc, C.; Rueba, E.; Schmid, R.; Kirchner, K. Organometallics 1999, 18, 4230-4233.
15. Grotjahn, D. B.; Gong, Y.; Zakharov, L. N.; Golen, J. A.; Rheingold, A. L. J. Am. Chem. Soc. 2006, 128, 438-453.
16. For examples of ligands we have made and tested here, see: Grotjahn, D. B.; Incarvito, C. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 2001, 40, 3884-3887.
17. Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232-12233.
18. Grotjahn, D. B.; Gong, Y.; DiPasquale, A. G.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2006, 25, 5693-5695.
19. See Supporting Information for details.
20. Trost, B. M.; Zhang, T. Org. Lett. 2006, 8, 6007-6010.
21. Schmidt, B. J. Mol. Catal. A: Chem. 2006, 254, 53-57.
22. Nelson, S. G.; Bungard, C. J.; Wang, K. J. Am. Chem. Soc. 2003, 125, 13000-13001.
23. Taskinen, E.; Virtanen, R. J. Org. Chem. 1977, 42, 1443-1449.
24. Placement of the base in the catalyst is crucial: adding 1-methyl-4-tert-butylimidazole to the 1-pentene isomerization by 1e made the reaction even slower.