Chiral dirhodium(II) catalysts with orthometalated aryl phosphine ligands: Synthesis and application for enantioselective C-H insertion of α-diazo ketones

Organometallics

Volumn 20, Issue 5, 2001, Pages 950-957

  Estevan, Francisco ^a   Herbst, Konrad ^a   Lahuerta, Pascual ^a   Barberis, Mario ^a   Pérez Prieto, Julia ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CHEMICAL BONDS; KETONES; RHODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CARBOCYCLES; CHIRAL DIRHODIUM CATALYSTS; DIAZO KETONES; ENANTIOMERS; ORTHOMETALATED ARYL PHOSPHINE LIGANDS;

ORGANOMETALLICS;

EID: 0035809956     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0010060     Document Type: Article

References (49)

1. (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
2. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
3. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
4. (a) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
5. (b) Doyle, M. P.; Dorow, R. L.; Buhro, W. E.; Griffin, J. H.; Tamblyn, W. H. Trudell, M. L. Organometallics 1984, 3, 44.
6. (c) Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305.
7. (d) Cai, L.; Mahmoud, H.; Han Ying Tetrahedron: Asymmetry 1999, 10, 411.
8. (e) Gettwert, V.; Krebs, F.; Maas, G. Eur. J. Org. Chem. 1999, 1213, 3.
9. For references on chemoselective transformations see: (a) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron 1992, 48, 9767.
10. (b) Brown, D. S.; Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669.
11. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
12. (d) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991.
13. (e) Moody, C. J.; Mowlen, T. J.; Marino, J. P., Jr.; Padwa, A. J. Org. Chem. 1994, 59, 2447.
14. (f) Estevan, F.; Lahuerta, P.; Pérez-Prieto, J.; Stiriba, S.-E.; Ubeda, M. A. Synlett 1995, 1121.
15. For references on regioselective transformations see: (g) Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1992, 33, 2709.
16. (h) Doyle, W. P.; Westrum, L. J.; Wolthius, W. N. E.; M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958.
17. For references on diastereo-selective transformations see: (i) Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
18. (j) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837
19. (a) McKervey, M. A. Chem. Commun. 1997, 983.
20. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
21. (c) Doyle, M. P.; Sulikowski, G. A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145.
22. (a) Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Daniel, K. L. Tetrahedron Lett. 1992, 33, 7819.
23. (b) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. L.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lync, V.; Ghosh, R. Recl. Trav. Chim. Pays-Bas 1995, 114, 163.
24. (a) Hashimoto, S.; Watanabe, N.; Ikegami, S. Synlett 1994, 353.
25. (b) Ferris, L.; Haigh, D.; Moody, C. J. Tetrahedron Lett. 1996, 37, 107.
26. Anada, M.; Watanabe, N.; Hashimoto, S. Chem. Commun. 1998, 1517.
27. Watanabe, N.; Anada, M.; Hashimoto, S.; Ikegami, S. Synlett 1994, 1031.
28. McKervey et al. have achieved good levels of enantioselectivity in cyclization of 2-diazo-1-1(2-alkoxyphenyl)propan-1-ones to give six-membered oxygen heterocycles by using chiral carboxylates: Ye, T.; Fernandez-Garcia, C.; McKervey, M. A. J. Chem. Soc., Perkin Trans. 1 1995, 1373.
29. Müller, P.; Polleux, P. Helv. Chim. Acta 1994, 77, 645.
30. (a) Doyle, M. P.; Eismont, M. Y.; Zhou, Q. L. Russ. Chem. Bull. 1997, 46, 955.
31. (b) Müller, P.; Maitrejean, E. Collect. Czech. Chem. Commun. 1999, 64, 1807.
32. Chakravarty, A. R.; Cotton, F. A.; Tocher, D. A.; Tocher, J. H. Organometallics 1985, 4, 8.
33. (a) Estevan, F.; Lahuerta, P.; Pérez-Prieto,J.; Sanaú, M.; Stiriba, S.-E.; Ubeda, M. A. Organometallics 1997, 16, 880.
34. (b) Estevan, F.; Lahuerta, P.; Pérez-Prieto, J.; Pereira, I.; Stiriba, S. E. Organometallics 1998, 17, 3442.
35. Taber, D. F.; Malcolm, S. C.; Bieger, S. K.; Lahuerta, P.; Stiriba, S.-E.; Pérez-Prieto, J.; Sanaú, M.; Monge, M. A. J. Am. Chem. Soc. 1999, 121, 860.
36. Boer, Th.; Backer, H. J. In Organic Synthesis; Rabjohn, N. Ed.; Wiley; New York, 1963; Vol. IV, p 250.
37. Taber, D. F.; Ruckle, R.E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.
38. Paquette, L. A.; Gilday, J. P.; Ra, C. S. J. Am. Chem. Soc. 1985, 109, 6858.
39. Similarly, rhodium(II) acetate catalyzes the intramolecular Buchner reaction of diazo compound 23 to produce the bicyclo [5.4.0]-undecane system: Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Tuladhar, S. M.; Twohig, M. F. J. Chem. Soc., Perkin Trans 1990, 1047.
40. (a) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; Van Basten, A.; Müller, P.; Polleaux, P. J. Am. Chem. Soc. 1994, 116, 4507.
41. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296.
42. (c) Taber, D. F.; Amedio. J. C., Jr.; Raman, K. J. Org. Chem. 1988, 53, 2984.
43. Doyle has suggested this alignment in α-diazo ketones to explain the relative inefficiency of chiral dirhodium carboxamidates for asymmetric cyclication of diazoketones compared to diazoacetates and diazoacetamides (see ref 11).
44. Lahuerta, P.; Payá, J.; Pellinghelli, M.; Tiripicchio, A. Inorg. Chem. 1992, 31, 1224.
45. Lahuerta, P.; Martinez-Mañez, R.; Payá, J.; Peris, E. Inorg. Chem. Acta 1990 173, 99.
46. Cupps, T. S.; Boutin, R. H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972.
47. Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Tuladhar, S. M.; Twohig, M. F. J. Chem. Soc., Perkin Trans. 1 1990, 1047.
48. Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821.
49. Ruppert, J. F.; White, J. D. J. Am. Chem. Soc. 1981, 103, 1808.