(Phosphino-oxazoline)copper(II) complexes as chiral catalysts for enantioselective Diels-Alder reactions

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 261-264

  Sagasser, Ingo ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; OXAZOLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS;

EID: 0032518889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10570-6     Document Type: Article

References (28)

1. 1 (a) Evans, D. A.; Miller, S. J.; Lecta, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
2. (b) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
3. (c) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757-5762.
4. (d) Johannsen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321-7328.
5. 2 (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
6. (b) Evans, D. A.; Kozlowski, M. C; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-7484.
7. 3 Bis(oxazoline)copper complexes are excellent catalysts for cyclopropanations (Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728; Müller, D.; Umbricht, B. W.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240) and aziridinations (Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329).
8. 3 Bis(oxazoline)copper complexes are excellent catalysts for cyclopropanations (Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728; Müller, D.; Umbricht, B. W.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240) and aziridinations (Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329).
9. 3 Bis(oxazoline)copper complexes are excellent catalysts for cyclopropanations (Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728; Müller, D.; Umbricht, B. W.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240) and aziridinations (Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329).
10. 3 Bis(oxazoline)copper complexes are excellent catalysts for cyclopropanations (Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008; Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728; Müller, D.; Umbricht, B. W.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240) and aziridinations (Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329).
11. 4 (a) Corey, E.J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 119, 728-729.
12. (b) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810.
13. (c) Desimoni, G.; Faita G.; Righetti P. P. Tetrahedron Lett. 1996, 37, 3027-3030.
14. 5 The requisite phosphino-oxazolines were readily prepared on a multi gram scale: Peer, M.; de Jong, J. C.; Kiefer, M.; Langer, T.; Rieck, H.; Schell, H.; Sennhenn, P.; Sprinz, J.; Steinhagen, H.; Wiese, B.; Helmchen, G. Tetrahedron 1996, 52, 7547-7583.
15. 6 Bulky dienophiles yielding mainly exo-adducts were recently reported: Powers, T. S.; Jiang, W.; Su, J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438-6439.
16. 2O, toluene, EtCN, DMF, ethyl acetate) were found to be inferior for this catalyst system.
17. 8 (a) Narasaka, K.; Inoue, M.; Okada, N. Chem. Lett. 1986, 1109;
18. (b) Gosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815-3818.
19. 2 at 0 °C. The resulting solution was allowed to warm to room temperature and stirred for 15 min. The cycloadduct was added and the solution was then heated at reflux overnight.
20. 2 at rt overnight according to a procedure of ref. 8b.
21. 11 The catalyst was prepared according to the procedure of Evans (ref. 1b).
22. 12 Allylic substitution: (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772;
23. (b) von Matt, P.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
24. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Transfer hydrogenation: Langer, Th.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Hydrosilylation of ketones: Langer, Th.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 1599-1602; Newman, L. M.; Williams, J. M. J.; McCague, R; Potter, G. A. Tetrahedron: Asymmetry 1996, 1597-1598. Heck reaction: Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 105, 218-220.
25. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Transfer hydrogenation: Langer, Th.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Hydrosilylation of ketones: Langer, Th.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 1599-1602; Newman, L. M.; Williams, J. M. J.; McCague, R; Potter, G. A. Tetrahedron: Asymmetry 1996, 1597-1598. Heck reaction: Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 105, 218-220.
26. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Transfer hydrogenation: Langer, Th.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Hydrosilylation of ketones: Langer, Th.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 1599-1602; Newman, L. M.; Williams, J. M. J.; McCague, R; Potter, G. A. Tetrahedron: Asymmetry 1996, 1597-1598. Heck reaction: Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 105, 218-220.
27. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Transfer hydrogenation: Langer, Th.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Hydrosilylation of ketones: Langer, Th.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 1599-1602; Newman, L. M.; Williams, J. M. J.; McCague, R; Potter, G. A. Tetrahedron: Asymmetry 1996, 1597-1598. Heck reaction: Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 105, 218-220.
28. (c) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. Transfer hydrogenation: Langer, Th.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Hydrosilylation of ketones: Langer, Th.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 1599-1602; Newman, L. M.; Williams, J. M. J.; McCague, R; Potter, G. A. Tetrahedron: Asymmetry 1996, 1597-1598. Heck reaction: Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem. 1996, 105, 218-220.