A modular approach to C1 and C3 chiral N-tripodal ligands for asymmetric catalysis

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3473-3475

  Bellemin Laponnaz, Stéphane ^a   Gade, Lutz H ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Asymmetric catalysis; Chirality; N,O ligands; Tripodal ligands

Indexed keywords

CATALYSIS; CATALYSTS; DERIVATIVES; RHODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

LIGANDS;

ETHANE;

1,1,1 TRIS(OXAZOLINYL)ETHANE DERIVATIVE; LIGAND; METAL COMPLEX; OXAZOLINE DERIVATIVE; RHODIUM DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037119729     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3473::AID-ANIE3473>3.0.CO;2-N     Document Type: Article

References (38)

1. A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
2. A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 33, 497.
3. a) R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005;
4. b) D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726;
5. c) D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232;
6. d) E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728.
7. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: a) F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159; b) M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769: c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1.
8. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: a) F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159; b) M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769: c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1.
9. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: a) F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159; b) M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769: c) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1.
10. a) Mukaiyama-Michael Reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480
11. b) cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125;
12. c) Henry reactions: C. Christensen, K. Juhl, K. A. Jørgensen, Chem. Commun. 2001, 2222;
13. d) Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2001, 66, 1009;
14. e) hetero-Diels-Alder reactions: D. A. Evans J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635;
15. f) molybdenum-catalyzed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141.
16. T. H. Chuang, J. M. Fang, C. Bolm, Synth. Commun. 2000, 30, 1627.
17. a) S. G. Kim, K. H. Ahn, Chem. Eur. J. 2000, 6. 3399;
18. b) S. G. Kim, K. H. Ahn, Tetrahedron Lett. 2001, 42. 4175;
19. c) S. G. Kim, K. H. Kim, J. Jung, S. K. Shin, K. H. Ahn, J. Am. Chem. Soc. 2002, 124, 591.
20. a) T. N. Sorrel, F. C. Pigge, P. S. White, Inorg. Chim. Acta 1993, 210, 87;
21. b) T. H. Chan, G. Z. Zheng, Can. J. Chem. 1997, 75, 629;
22. c) K. Kawasaki, T. Katsuki, Tetrahedron 1997, 53, 6337;
23. d) Y. Kohmura, T. Katsuki, Tetrahedron Lett. 2000, 41, 3941.
24. C. Moberg, Angew. Chem. 1998, 110, 210; Angew. Chem. Int. Ed. 1998, 37, 248.
25. C. Moberg, Angew. Chem. 1998, 110, 210; Angew. Chem. Int. Ed. 1998, 37, 248.
26. S. Bellemin-Laponnaz, L. H. Gade, Chem. Commun. 2002, 1286.
27. The bisoxazoline starting materials can be easily synthesized by using the procedure reported by Denmark and Stiff: S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875.
28. 2-bromooxazolines can be obtained from 2 H-oxazolines, see: A. I. Meyers, K. A. Novachek, Tetrahedron Lett. 1996, 37. 1747. For an introduction to the chemistry of 2-oxazolines in general, see: T. G. Gant. A. I. Meyers, Tetrahedron 1994, 50, 2297.
29. 2-bromooxazolines can be obtained from 2 H-oxazolines, see: A. I. Meyers, K. A. Novachek, Tetrahedron Lett. 1996, 37. 1747. For an introduction to the chemistry of 2-oxazolines in general, see: T. G. Gant. A. I. Meyers, Tetrahedron 1994, 50, 2297.
30. a) M. P. Doyle, M. N. Protopopova, Tetrahedron 1998, 54, 7919;
31. b) Comprehensive Asymmetric Catalysis (Eds.: A. Pfaltz, H. Yamamoto. E. N. Jacobsen), Springer, Heidelberg, 1999, chap. 16.
32. a) R. E. Lowenthal. S. Masamune,. Tetrahedron Lett. 1991, 32, 7373;
33. b) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430.
34. b) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430.
35. Very recently Pérez et al. reported a copper-homoscorpionate catalyst with high diastereoselectivity toward the cis isomer, see: a) M. M. Díaz-Requejo, A. Caballero, T. R. Belderraín, M. C. Nicasio, S. Trofimenko, P. D. Pérez, J. Am. Chem. Soc. 2002, 124, 978: b) b) M. M. Díaz-Requejo, T. R. Belderraín, S. Trofimenko, P. D. Pérez, J. Am. Chem. Soc. 2001, 123, 3167.
36. Very recently Pérez et al. reported a copper-homoscorpionate catalyst with high diastereoselectivity toward the cis isomer, see: a) M. M. Díaz-Requejo, A. Caballero, T. R. Belderraín, M. C. Nicasio, S. Trofimenko, P. D. Pérez, J. Am. Chem. Soc. 2002, 124, 978: b) b) M. M. Díaz-Requejo, T. R. Belderraín, S. Trofimenko, P. D. Pérez, J. Am. Chem. Soc. 2001, 123, 3167.
37. Nonius OpenMoleN, Interactive Structure Solution, Delft, 1997.
38. D. T. Cromer, J. T. Waber, International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, 1974.