Asymmetric catalysis of the Diels-Alder reaction using dicationic zirconocene complexes

Organometallics

Volumn 19, Issue 6, 2000, Pages 947-949

  Bondar, Georgiy V ^a   Aldea, Raluca ^a   Levy, Christopher J ^a   Jaquith, James B ^a   Collins, Scott ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3743099792     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990759n     Document Type: Article

References (21)

1. For a relatively recent review, see: Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262 and references therein.
2. (a) Jaquith, J. B.; Guan, J.; Wang, S.; Collins, S. Organometallics 1995, 14, 1079.
3. For other applications of group 4 metallocene bis-(triflate) complexes see: (b) Odenkirk, W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1995, 1181 and references therein. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570 and references therein. (d) Li, S.; Bondar, G. V.; Levy, C. J.; Collins, S. J. Org. Chem. 1998, 63, 1885.
4. For other applications of group 4 metallocene bis-(triflate) complexes see: (b) Odenkirk, W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1995, 1181 and references therein. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570 and references therein. (d) Li, S.; Bondar, G. V.; Levy, C. J.; Collins, S. J. Org. Chem. 1998, 63, 1885.
5. For other applications of group 4 metallocene bis-(triflate) complexes see: (b) Odenkirk, W.; Bosnich, B. J. Chem. Soc., Chem. Commun. 1995, 1181 and references therein. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570 and references therein. (d) Li, S.; Bondar, G. V.; Levy, C. J.; Collins, S. J. Org. Chem. 1998, 63, 1885.
6. For the use of other cyclopentadienyl (and related organometallic) complexes as catalysts for Diels-Alder reactions see e.g.: (a) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (b) Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Tetrahedron Lett. 1997, 1351. (c) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Tetrahedron Lett. 1997, 2347. (d) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; Lopez-Ram, M. P.; Oro, L.; Vega, C.; Viguri, F. Tetrahedron. Lett. 1997, 2351.
7. For the use of other cyclopentadienyl (and related organometallic) complexes as catalysts for Diels-Alder reactions see e.g.: (a) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (b) Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Tetrahedron Lett. 1997, 1351. (c) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Tetrahedron Lett. 1997, 2347. (d) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; Lopez-Ram, M. P.; Oro, L.; Vega, C.; Viguri, F. Tetrahedron. Lett. 1997, 2351.
8. For the use of other cyclopentadienyl (and related organometallic) complexes as catalysts for Diels-Alder reactions see e.g.: (a) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (b) Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Tetrahedron Lett. 1997, 1351. (c) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Tetrahedron Lett. 1997, 2347. (d) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; Lopez-Ram, M. P.; Oro, L.; Vega, C.; Viguri, F. Tetrahedron. Lett. 1997, 2351.
9. For the use of other cyclopentadienyl (and related organometallic) complexes as catalysts for Diels-Alder reactions see e.g.: (a) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (b) Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Tetrahedron Lett. 1997, 1351. (c) Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Tetrahedron Lett. 1997, 2347. (d) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; Lopez-Ram, M. P.; Oro, L.; Vega, C.; Viguri, F. Tetrahedron. Lett. 1997, 2351.
10. Jaquith, J. B.; Levy, C. J.; Bondar, G. V.; Wang, S.; Collins, S. Organometallics 1998, 17, 914.
11. For work on dicationic, zirconocene complexes see: (a) Jordan, R. F.; Echols, S. F. Inorg. Chem. 1987, 26, 383. (b) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718. (c) Thewalt, U.; Lasser, W. J. Organomet. Chem. 1984, 276, 341. (d) Thewalt, U.; Klein, H. P. J. Organomet. Chem. 1980, 194, 297.
12. For work on dicationic, zirconocene complexes see: (a) Jordan, R. F.; Echols, S. F. Inorg. Chem. 1987, 26, 383. (b) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718. (c) Thewalt, U.; Lasser, W. J. Organomet. Chem. 1984, 276, 341. (d) Thewalt, U.; Klein, H. P. J. Organomet. Chem. 1980, 194, 297.
13. For work on dicationic, zirconocene complexes see: (a) Jordan, R. F.; Echols, S. F. Inorg. Chem. 1987, 26, 383. (b) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718. (c) Thewalt, U.; Lasser, W. J. Organomet. Chem. 1984, 276, 341. (d) Thewalt, U.; Klein, H. P. J. Organomet. Chem. 1980, 194, 297.
14. For work on dicationic, zirconocene complexes see: (a) Jordan, R. F.; Echols, S. F. Inorg. Chem. 1987, 26, 383. (b) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718. (c) Thewalt, U.; Lasser, W. J. Organomet. Chem. 1984, 276, 341. (d) Thewalt, U.; Klein, H. P. J. Organomet. Chem. 1980, 194, 297.
15. This idea was also suggested to us by Prof. D. F. Taber (University of Delaware).
16. Brookhart, M.; Grant, B.; Volpe, A. F. Organometallics 1992, 11, 3290 and references therein. We thank Prof. Richard Jordan (University of Chicago) for suggesting the use of this material.
17. 2N).
18. Under these conditions, complex 5 is contaminated with a small amount of a complex (ca. 5 mol %) containing coordinated ether. Coordinated ether can be removed by the use of an excess of 1 (ca. 5 equiv) during preparation of 5, followed by removal of solvent in vacuo. Unfortunately, separation of 5 from excess 1 by attempted crystallization leads to the formation of oils which are contaminated by 1.
19. 1H NMR experiments suggest the latter scenario is likely.
20. For efficient resolutions of this ansa-metallocene see: Chin, B.; Buchwald, S. L. J. Org. Chem. 1997, 62, 2267 and references therein.
21. 4