Asymmetric intermolecular C-H functionalization of benzyl silyl ethers mediated by chiral auxiliary-based aryldiazoacetates and chiral dirhodium catalysts

Journal of Organic Chemistry

Volumn 70, Issue 26, 2005, Pages 10737-10742

  Davies, Huw M L ^a   Hedley, Simon J ^a   Bohall, Brooks R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; DERIVATIVES; RHODIUM; STEREOCHEMISTRY;

C-H FUNCTIONALIZATION; CHIRAL CATALYSTS; ENANTIOSELECTIVITY;

ETHERS;

ACETIC ACID DERIVATIVE; BENZYL SILYL ETHER DERIVATIVE; CARBON; DIAZONIUM COMPOUND; ETHER DERIVATIVE; FUNCTIONAL GROUP; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROLINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMISTRY; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY;

EID: 29944440950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051747g     Document Type: Article

References (46)

1. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
2. (a) Davies, H. M. L.; Antoulinakis, E. J. Organomet. Chem. 2001, 617, 47.
3. (b) Davies, H. M. L. J. Mol. Catal. A: Chem. 2002, 189, 125.
4. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6896.
5. Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287.
6. (a) Davies, H. M. L.; Beckwith, R. E. J.; Antoulinakis, E. G.; Jin, Q. J. Org. Chem. 2003, 68, 6126.
7. (b) Davies, H. M. L.; Antoulinakis, E. G. Org. Lett. 2000, 2, 4153.
8. (c) Davies, H. M. L.; Antoulinakis, E. G.; Hansen, T. Org. Lett. 1999, 1, 383.
9. (a) Davies, H. M. L.; Venkataramani, C.; Hansen, T.; Hopper, D. W. J. Am. Chem. Soc. 2003, 125, 6462.
10. (b) Davies, H. M. L.; Hansen, T.; Hopper, D.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509.
11. (c) Davies, H. M. L.; Venkataramani, C. Org. Lett. 2001, 3, 1773.
12. (d) Davies, H. M. L.; Venkataramani, C. Angew. Chem., Int. Ed. 2002, 41, 2197.
13. Davies, H. M. L.; Ren, P. J. Am. Chem. Soc. 2001, 123, 2071.
14. Davies, H. M. L.; Ren, P.; Jin, Q. Org. Lett. 2001, 3, 3587.
15. (a) Davies, H. M. L.; Ren, P.; Jin, Q.; Kovalevsky, A. Y. J. Org. Chem. 2002, 67, 4165.
16. (b) Davies, H. M. L.; Jin, Q. Tetrahedron: Asymmetry 2003, 14, 941.
17. Ward, R. S. Nat. Prod. Rep. 1999, 16, 75.
18. Relative stereochemistry was assigned on the basis of the distinctive proton NMR chemical-shift differences: Davies, H. M. L.; Ren, P. Tetrahedron Lett. 2001, 42, 3149. Absolute stereochemistry was determined later by X-ray crystallographic analysis of compound 23 (see ref 23 and the Supporting Information), and the configuration of the other reaction products was assigned by analogy from these data.
19. Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
20. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R., Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468.
21. (a) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
22. (b) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095.
23. (c) Davies, H. M. L.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641.
24. (d) He, M.; Tanimori, S.; Ohira, S.; Nakayama, M. Tetrahedron 1997, 53, 13307.
25. (e) Moore, J. D.; Hanson, P. R. Tetrahedron: Asymmetry 2003, 14, 873.
26. (f) Moore, J. D.; Sprott, K. T.; Wrobleski, A. D.; Hanson, P. R. Org. Lett. 2002, 4, 2357.
27. (g) Ye, T.; McKervey, M. A.; Bandes, B.; Doyle, M. P. Tetrahedron Lett. 1994, 35, 7269.
28. (h) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1994, 35, 9549.
29. (i) Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855.
30. (j) Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630.
31. (k) Doyle, M. P.; Yan, M. Tetrahedron Lett. 2002, 43, 5929.
32. (l) Kurosawa, W.; Kan, T.; Fukuyama, T. Synlett 2003, 1028.
33. Kurosawa, W.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 8112.
34. (n) Kurosawa, W.; Kobayashi, H.; Kan, T.; Fukuyama, T. Tetrahedron 2004, 60, 9615.
35. Davies, H. M. L.; Kong, N. Tetrahedron Lett. 1997, 38, 4203.
36. (a) Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1990, 31, 5173.
37. (b) Takahashi, T.; Tsutsui, H.; Tamura, M.; Kitagaki, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 2001, 1604.
38. (c) Anada, M.; Hashimoto, S. Tetrahedron Lett. 1998, 39, 79.
39. (d) Anada, M.; Watanabe, N.; Hashimoto, S. Chem. Commun. 1998, 1517.
40. (e) Hashimoto, S.; Watanabe, N.; Ikegami, S. Synlett 1994, 353.
41. Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
42. 4-catalyzed reaction was demonstrated to proceed in 73% yield, with a 79:21 ratio of C-H insertion product to cyclopropane product, with the former isolated with poor diastereoselectivity but excellent enantioselectivity (93% ee, R enantiomer: ref 8).
43. Müller, P.; Bernardinelli, G.; Allenbach, Y. F.; Ferri, M.; Flack, H. D. Org. Lett. 2004, 6, 1725.
44. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987.
45. Davies, H. M. L.; Hansen, T.; Rutberg, J.; Bruzinski, P. R. Tetrahedron Lett. 1997, 38, 1741.
46. The crystal structure has been deposited at the Cambridge Crystallographic Data Centre, and the deposition number CCDC 277546 has been allocated (Gerlits, O. O.; Coppens, P. Personal communication).