Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/siloxy-cope rearrangement

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9241-9247

  Davies, Huw M L ^a   Beckwith, Rohan E J ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CARBON; CATALYSIS; CHEMICAL BONDS; ETHERS; HYDROGEN; STEREOCHEMISTRY;

ASYMMETRIC REACTIONS; SILOXY-COPE REARRANGEMENT; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ACETIC ACID DERIVATIVE; CARBON; ETHER DERIVATIVE; HYDROGEN; ORGANIC COMPOUND; RHODIUM DERIVATIVE; TETRAKIS[N (4 DODECYLBENZESULFONYL)PROLINATE]DIRHODIUM; UNCLASSIFIED DRUG; VINYLDIAZOACETATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COPE REARRANGEMENT; DECOMPOSITION; MICROWAVE RADIATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; THERMAL ANALYSIS;

EID: 10844263413     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048429m     Document Type: Article

References (56)

1. For selected reviews on other methods for C-H activation, see: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
2. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 28, 1698.
3. (c) Arndsten, B. A.; Bergman, R. G. Science 1995, 270, 1970.
4. (d) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
5. (e) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
6. (f) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
7. For recent examples, see: (a) Nokami, J.; Ohga, M.; Nakamoto, H.; Matsubara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. Soc. 2001, 123, 9168.
8. (b) Allin, S. M.; Baird, R. D.; Lins, R. J. Tetrahedron Lett. 2002, 43, 4195.
9. (c) Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9434.
10. For a recent review of [3,3]-sigmatropic rearrangements, see: Nubbemeyer, U. Synthesis 2003, 961 and references therein.
11. For reviews on the siloxy-Cope rearrangement of chiral aldol products, see: (a) Schneider, C.; Rehfeuter, M. Tetrahedron 1997, 53, 133.
12. (b) Schneider, C. Synlett 2001, 1079.
13. (a) Schneider, C.; Rehfeuter, M. Synlett 1996, 212.
14. (b) Schneider, C. Synlett 1997, 815.
15. (c) Schneider, C. Eur. J. Org. Chem. 1998, 1661.
16. (d) Schneider, C.; Börner, C. Synlett 1998, 652.
17. (e) Schneider, C.; Rehfeuter, M. Tetrahedron Lett. 1998, 39, 9.
18. (f) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850.
19. (g) Schneider, C.; Börner, C.; Schuffenhauser, A. Eur. J. Org. Chem. 1999, 3353.
20. (h) Schneider, C.; Schuffenhauser, A. Eur. J. Org. Chem. 2000, 73.
21. (i) Schneider, C.; Reese, O. Angew. Chem., Int. Ed. 2000, 39, 2948.
22. (J) Schneider, C.; Reese, O. Synthesis 2000, 1689.
23. (k) Schneider, C.; Reese, O. Chem. Eur. J. 2002, 8, 2585.
24. Black, W. C.; Giroux, A.; Greidanus; G. Tetrahedron Lett. 1996, 37, 4471.
25. (a) Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8895.
26. (b) Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8899.
27. For a review on the catalytic enantioselective C-H activation chemistry of diazo compounds, see: Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
28. For a recent review on the intermolecular C-H activation chemistry of diazo compounds, see: Davies, H. M. L. J. Mol. Catal. A: Chem. 2002, 189, 125.
29. For recent examples of enantioselective intermolecular C-H activation of diazo compounds, see: (a) Davies, H. M. L.; Jin, Q. Org. Lett. 2004, 6, 1769.
30. (b) Davies, H. M. L.; Hopper, D. W.; Hansen, T.; Liu, X.; Childers, S. R. Biorg. Med. Chem. Lett. 2004, 14, 1799.
31. (c) Davies, H. M. L.; Venkataramani, C.; Hansen, T.; Hopper, D. W. J. Am. Chem. Soc. 2003, 125, 6462.
32. (d) Davies, H. M. L.; Beckwith, R. E. J.; Antoulinakis, E. G.; Jin, Q. J. Org. Chem. 2003, 68, 6126.
33. (e) Davies, H. M. L.; Yang, J. Adv. Synth. Catal. 2003, 345, 1133.
34. (f) Davies, H. M. L.; Jin, Q. Tetrahedron: Asymmetry 2003, 14, 941.
35. (g) Davies, H. M. L.; Walji, A. M. Org. Lett. 2003, 5, 479.
36. Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. S. Tetrahedron Lett. 1998, 39, 4417.
37. (a) Davies, H. M. L.; Stafford, D. G.; Hansen, T. Org. Lett. 1999, 1, 233.
38. (b) Davies, H. M. L.; Stafford, D. G.; Hansen, T.; Churchill, M. R.; Keil, K. M, Tetrahedron Lett. 2000, 41, 2035.
39. (c) Davies, H. M. L.; Jin, Q. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5472.
40. (d) Davies, H. M. L.; Jin, Q. J. Am. Chem. Soc. 2004, 126, 10862.
41. (a) Hill, R. K.; Gilman, N. W. J. Chem. Soc., Chem. Commun. 1967, 619.
42. (b) Doering, W. von E.; Toscano, V. G.; Beasley, G. H. Tetrahedron 1971, 27, 5299.
43. Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987.
44. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
45. Doyle, M. P.; Davies, S. B.; Hu, W. Org. Lett. 2000, 2, 1145.
46. Davies, H. M. L.; Panaro, S. A, Tetrahedron Lett. 1999, 40, 5287.
47. Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
48. The X-ray crystallographic data have been submitted to the Cambridge Structure Database [Gerlits, O. O.; Coppens, P. Private Communication (1078), 2004], Deposition no. CCDC 237997.
49. For a review on microwave assisted organic synthesis see: Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
50. (a) Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 2002, 1850.
51. (b) Leadbeater, N. E.; Torenius, H. M. J. Org. Chem. 2002, 67, 3145.
52. Carboflon heating inserts (part number SP-1125) were obtained from CEM. For an example of the use of a similar heating additive in organic synthesis, see: Barriault, L.; Denissova, I. Org. Lett. 2002, 4, 1371.
53. Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1986, 118, 6897.
54. (a) Stetter, H.; Kuhlmann, H. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1991; Vol. 40, p 407.
55. (b) Ciganek, E. Synthesis 1995, 1311.
56. (c) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.