Investigation of the scope of a Co-mediated O → C ring-contraction

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3467-3477

  Meek, Simon J ^a   Pradaux, Fabienne ^a   Demont, Emmanuel H ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPOUNDS; FURAN RESINS; PROPANE; SUBSTRATES; SYNTHESIS (CHEMICAL);

CARBON RING CONTRACTION; CYCLOPROPANES; DIHYDROFURANS; DIHYDROPYRANS;

ORGANIC COMPOUNDS;

ALUMINUM; CARBON; CARBONYL DERIVATIVE; COBALT; CYCLOPROPANE; OXYGEN; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; RING CONTRACTION;

CARBON; CHEMISTRY, ORGANIC; COBALT; CYCLOPROPANES; MODELS, CHEMICAL; OXYGEN; PYRANS;

EID: 34247577450     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0701132     Document Type: Article

References (56)

1. Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; lohn Wiley & Sons: New York, 1994; Chapter 11; p 677.
2. (a) Robertson, J. M; Todd, G. Chem. Ind. (London) 1953, 437,
3. J. Chem. Soc. 1955, 1254.
4. (b) Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1963, 85, 362.
5. (c) Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485.
6. (d) For a recent enantioselective synthesis, see Liu, D.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 8160.
7. (a) Tumlinson, J. H.; Hardee, D. D.; Gueldner, R. C.; Thompson, A. C.; Hedlin, P. A.; Minyard, J. P. Science 1969, 166, 1010.
8. For examples of racemic and optically active grandisol, see (b) Mori, K.; Miyake, M. Tetrahedron 1987, 43, 2229.
9. (c) Kim, D.; Kwak, Y. S.; Shin, K. J. Tetrahedron Lett. 1994, 35, 9211.
10. (d) Martín, T.; Rodriguez, C. M.; Martín, V. S. Tetrahedron Asymm. 1995, 6, 1151.
11. (a) Anderson, J. R.; Briant, C. E.; Edwards, R. L.; Mabelis, R. P.; Poyser, J. P.; Spencer, H.; Whalley, A. J. S. J. Chem. Soc., Chem. Commun. 1984, 405.
12. (b) Sugimura, T.; Paquette, L. J. Am. Chem. Soc. 1986, 108, 3841.
13. (c) Sugimura, T.; Paquette, L. J. Am. Chem. Soc. 1987, 109, 3017.
14. (a) Pulici, M.; Sugawara, F.; Koshino, H.; Uzawa, J.; Yoshida, S.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1996, 61, 2122.
15. (b) Pulici, M.; Sugawara, F.; Koshino, H.; Okada, G.; Esumi, Y.; Uzawa, J.; Yoshida S. Phytochemistry 1997, 46, 313.
16. Wichlacz, M.; Ayer, W. M.; Trifonov, L. S.; Chakraarty, P.; Khasa, D. J. Nat. Prod. 1999, 62, 484.
17. (a) Nemeto, H.; Fukumoto, K. Synlett 1997, 863.
18. (b) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449.
19. Haufe, G. In Methods of Organic Chemistry; DeMeijere, A., Ed.; Houben-Weyl; George Thieme Verlag: Stuttgart, Germany, 1997; Vol E17e, pp 317-367.
20. (a) Menicagli, R.; Malanga, C.; Lardicci, L.; Tinucci, L. Tetrahedron Lett. 1980, 21, 4525.
21. (b) Menicagli, R.; Malanga, C.; Lardicci, L. J. Org. Chem. 1982, 47, 2288.
22. (c) Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 48, 2789.
23. (d) Malanga, C.; Menicagli, R.; Pecunioso, A.; Lardicci, L. Gazz. Chim. Ital. 1991, 121, 17.
24. (a) Ito, H.; Motoki, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1993, 115, 8835.
25. (b) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1993, 34, 7639.
26. (c) Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299.
27. (d) Paquette, L. A.; Cunière, N. Org. Lett. 2002, 4, 1927.
28. (e) Paquette, L. A.; Kim, I. H.; Cunière, N. Org. Lett. 2003, 5, 221.
29. (f) Paquette, L. A.; Zhang, Y.; Org. Lett. 2005, 7, 511.
30. (g) Paquette, L. A. J. Organomet. Chem. 2006, 691, 2083.
31. (h) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
32. (i) Swanson, D. R.; Negishi, E. Organometallics 1991, 10, 825.
33. Aurrecoechea, J. M.; López, B.; Arrate, M. J. Org. Chem. 2000, 65, 6493.
34. For an overview of O → C rearrangements see Meek, S. J.; Harrity, J. P. A. Tetrahedron 2007, 63, 3081.
35. (a) Carbery, D. R.; Reignier, S.: Myatt, J. W.; Miller, N. D.; Harrity, J. P. A. Angew. Chem., Int. Ed. 2002, 41, 2584.
36. (b) Carbery, D. R.; Miller, N. D.; Harrity, J. P. A. Chem. Commun. 2002, 1546.
37. (c) Carbery, D. R.; Reignier, S.; Miller, N. D.; Adams, H.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4392.
38. (d) Meek, S. J.; Pradaux, F.; Carbery, D. R.; Demont, E. H.; Harrity, J. P. A. J. Org. Chem. 2005, 70, 10046.
39. Taskinen, E. Tetrahedron 1978, 34, 433.
40. Meek, S. J.; Pradaux, F.; Demont, E. H.; Harrity, J. P. A. Org. Lett. 2006, 8, 5597.
41. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207.
42. (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 685.
43. (c) Green, J. R. Curr. Org. Chem. 2001, 5, 809.
44. (d) Teobald, B. J. Tetrahedron 2002, 58, 4133.
45. (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
46. (b) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.
47. (c) Castellino, S.; Dwight, W. J. J. Am. Chem. Soc. 1993, 115, 2986.
48. 9b but our proposed mechanism is based on NMR and theoretical studies of intermediate Co-stabilized propargylic cations: (a) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
49. (b) Pfletschinger, A.; Koch, W.; Schmalz, H.-G. Chem. Eur. J. 2001, 7, 5325.
50. Jones, G. B.; Wright, J. M.; Rush, T. M.; Plourde, G. W., II; Kelton, T. F.; Mathews, J. E.; Huber, R. S.; Davidson, J. P. J. Org. Chem. 1997, 62, 9379.
51. For the use of related Co-alkyne containing cyclopropanes in cycloaddition reactions see (a) Christie, S. D. R.; Davoile, R. J.; Elsegood, M. R. J.; Fryatt, R.; Jones, R. C. F.; Pritchard, G. J. Chem. Commun. 2004, 2474.
52. (b) Christie, S. D. R.; Davoile, R. J.; Jones, R. C. F. Org. Biomol. Chem. 2006, 4, 2683.
53. (a) Hutton, H. M.; Schaefer, T. Can. J. Chem. 1962, 40, 875.
54. (b) Wiberg, K. B.; Nist, B. J. J. Am. Chem. Soc. 1963, 85, 2788.
55. (c) Wiberg, K. B.; Bareth, D. E.; Schertler, P. J. Org. Chem. 1973, 38, 378.
56. 13d