Chiral Cyclopentadienyl-Iron and -Ruthenium Lewis Acids Containing the Electron-Poor BIPHOP-F Ligand: A Comparison as Catalysts in an Asymmetric Diels-Alder Reaction

Advanced Synthesis and Catalysis

Volumn 343, Issue 1, 2001, Pages 51-56

  Kündig, E Peter ^a   Saudan, Christophe M ^a   Viton, Florian ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric catalysis; Cycloadditions; Iron; Lewis acids; Ruthenium

Indexed keywords

EID: 0037847918     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010129)343:1<51::AID-ADSC51>3.0.CO;2-N     Document Type: Article

References (24)

1. Handbook of Lewis Acids - Application in Organic Synthesis, Ed. H. Yamamoto, Wiley-VCH, Weinheim, 2000.
2. (a) B. Bosnich, Aldrichimica Acta 1998, 31, 76-83;
3. [1], 597-652.
4. (a) M. E. Bruin, E. P. Kündig, Chem. Commun. 1998, 2635-2636;
5. (b) E. P. Kündig, C. M. Saudan, G. Bernardinelli, Angew. Chem. Int. Ed. 1999, 38, 1220-1223.
6. Reviews: (a) L. C. Dias, J. Braz. Chem. Soc. 1997, 8, 289-332; (b) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401. For recent examples of chiral catalysts for this reaction, see: (c) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594; (d) J. W. Faller, J. Parr, Organometallics 2000, 19, 1829-1832; (e) G. B. Jones, M. Guzel, Tetrahedron: Asymmetry 2000, 11, 1267-1271.
7. Reviews: (a) L. C. Dias, J. Braz. Chem. Soc. 1997, 8, 289-332; (b) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401. For recent examples of chiral catalysts for this reaction, see: (c) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594; (d) J. W. Faller, J. Parr, Organometallics 2000, 19, 1829-1832; (e) G. B. Jones, M. Guzel, Tetrahedron: Asymmetry 2000, 11, 1267-1271.
8. Reviews: (a) L. C. Dias, J. Braz. Chem. Soc. 1997, 8, 289-332; (b) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401. For recent examples of chiral catalysts for this reaction, see: (c) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594; (d) J. W. Faller, J. Parr, Organometallics 2000, 19, 1829-1832; (e) G. B. Jones, M. Guzel, Tetrahedron: Asymmetry 2000, 11, 1267-1271.
9. Reviews: (a) L. C. Dias, J. Braz. Chem. Soc. 1997, 8, 289-332; (b) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401. For recent examples of chiral catalysts for this reaction, see: (c) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594; (d) J. W. Faller, J. Parr, Organometallics 2000, 19, 1829-1832; (e) G. B. Jones, M. Guzel, Tetrahedron: Asymmetry 2000, 11, 1267-1271.
10. Reviews: (a) L. C. Dias, J. Braz. Chem. Soc. 1997, 8, 289-332; (b) E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401. For recent examples of chiral catalysts for this reaction, see: (c) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594; (d) J. W. Faller, J. Parr, Organometallics 2000, 19, 1829-1832; (e) G. B. Jones, M. Guzel, Tetrahedron: Asymmetry 2000, 11, 1267-1271.
11. S. R. Bahr, P. Boudjouk, J. Org. Chem. 1992, 57, 5545-5547.
12. For precedence, see: (a) P. V. Bonnesen, C. L. Puckett, R. V. Honeychuck, W. H. Hersh, J. Am. Chem. Soc. 1989, 111, 6070-6081; (b) B. J. Boone, D. P. Klein, J. W. Seyler, N. Q. Méndez, A. M. Arif, J. A. Gladysz, J. Am. Chem. Soc. 1996, 118, 2411-2421.
13. For precedence, see: (a) P. V. Bonnesen, C. L. Puckett, R. V. Honeychuck, W. H. Hersh, J. Am. Chem. Soc. 1989, 111, 6070-6081; (b) B. J. Boone, D. P. Klein, J. W. Seyler, N. Q. Méndez, A. M. Arif, J. A. Gladysz, J. Am. Chem. Soc. 1996, 118, 2411-2421.
14. 3PI (-78°C → -20°C).
15. 2, -20°C.
16. D. A. Evans, J. A. Murry, P. von Matt, R. D. Norcross, S. J. Miller, Angew. Chem. Int. Ed. Engl. 1995, 34, 798-800.
17. For a literature precedent of this technique, see: A. Macchioni, G. Bellachioma, G. Cardaci, G. Cruciani, E. Foresti, P. Sabatino, C. Zuccaccia, Organometallics 1998, 17, 5549-5556.
18. K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 1989, 54, 1481-1483.
19. From elegant studies, Albinati and Pregosin et al. have concluded that the ligand meta dialkyl effect results in a number of catalysts in a more rigid chiral pocket which in turn can lead to marked improvement of observed enantioselectivities; (a) G. Trabesinger, A. Albinati, N. Feiken, R. W. Kunz, P. S. Pregosin, A. Tschoerner, J. Am. Chem. Soc. 1997, 119, 6315-6323; (b) K. Selvakumar, A. Valentini, P. S. Pregosin, A. Albinati, F. Eisentraeger, Organometallics, 2000, 19, 1299-1307.
20. From elegant studies, Albinati and Pregosin et al. have concluded that the ligand meta dialkyl effect results in a number of catalysts in a more rigid chiral pocket which in turn can lead to marked improvement of observed enantioselectivities; (a) G. Trabesinger, A. Albinati, N. Feiken, R. W. Kunz, P. S. Pregosin, A. Tschoerner, J. Am. Chem. Soc. 1997, 119, 6315-6323; (b) K. Selvakumar, A. Valentini, P. S. Pregosin, A. Albinati, F. Eisentraeger, Organometallics, 2000, 19, 1299-1307.
21. H. Sasaki, R. Irie, T. Hamada, K. Suzuki, T. Katsuki, Tetrahedron 1994, 50, 11827-11838.
22. (a) M. Fild, O. Glemser, I. Hollenberg, Z. Naturforsch., Teil B 1966, 21, 920-923;
23. (b) R. Ali, K. B. Dillon, J. Chem. Soc., Dalton Trans. 1990, 2593-2596.
24. For a highly enantioselective organocatalytic Diels-Alder reaction, see: K. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.