Structure-reactivity in relationships in oxidative carbon-carbon bond forming reactions: A mild and efficient approach to stereoselective syntheses of 2,6-disubstituted tetrahydropyrones

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12596-12603

  Wang, Lijun ^a   Seiders II, John R ^a   Floreancig, Paul E ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMMONIUM COMPOUNDS; BENZENE; CARBON; CHEMICAL BONDS; ETHERS; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CLEAVAGE REACTIONS; CYCLIZATION; HOMOBENZYLIC ETHERS; STEREOCONTROL;

KETONES;

ACETIC ACID; AMMONIUM NITRATE; BASE; BENZYL DERIVATIVE; CARBENE; CARBON; CATION; CERIC AMMONIUM NITRATE; CERIUM; ETHER DERIVATIVE; LEWIS ACID; NATURAL PRODUCT; OXIDIZING AGENT; OXOCARBENIUM ION; OXYGEN; PYRONE DERIVATIVE; TETRAHYDROPYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BOND CLEAVAGE; COVALENT BOND; CYCLIZATION; DISSOCIATION; NUCLEOPHILE; OXIDATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CYCLIZATION; FREE RADICALS; OXIDATION-REDUCTION; PYRONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4644339111     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046125b     Document Type: Article

References (77)

1. For reviews of radical cation reactivity patterns, see: (a) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550.
2. (b) Baciocchi, E.; Bietti, M.; Lanzalunga, O. Acc. Chem. Res. 2000, 33, 243.
3. (c) Schmittel, M.; Ghorai, M. K. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2.
4. Yoshida, J.-i.; Nishiwaki, K. J. Chem. Soc., Dalton Trans. 1998, 2589.
5. Reed, R. C.; Wightman, R. M. In Encyclopedia of Electrochemistry of the Elements; Bard, A. J., Ed.; Marcel Dekker: New York, 1984; Vol. 15.
6. For excellent tabulations of bond dissociation energies in organic molecules, see: (a) Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
7. (b) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
8. Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc, 1988, 110, 132.
9. (a) Dinnocenzo, J. P.; Simpson, T. R.; Zuilhof, H.; Todd, W. P.; Heinrich, T. J. Am. Chem. Soc. 1997, 119, 987.
10. (b) Dinnocenzo, J. P.; Zuilhof, H.; Lieberman, D. R.; Simpson, T. R.; McKetchney, M. W. J. Am. Chem. Soc. 1997, 119, 994.
11. (c) Herbertz, T.; Roth, H. D. J. Org. Chem. 1999, 64, 3708.
12. (a) Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, I. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 119, 1876.
13. (b) Arnold, D. R.; Du, X.; Chen, J. Can. J. Chem. 1995, 73, 307.
14. Freccero, M.; Pratt, A.; Albini, A.; Long, C. J. Am. Chem. Soc. 1998, 120, 284.
15. Kumar, V. S.; Floreancig, P. E. J. Am. Chem. Soc. 2001, 123, 3842.
16. Aubele, D. L.; Floreancig, P. E. Org. Lett. 2002, 4, 3443.
17. The directionality of the mesolytic cleavage is consistent with alkoxyalkyl and amidoalkyl radicals having significantly lower oxidation potentials than benzyl radicals (ref 5).
18. Kumar, V. S.; Aubele, D. L.; Floreancig, P. E. Org. Lett. 2002, 4, 2849.
19. Rech, J. C.; Floreancig, P. E. Org. Lett. 2003, 5, 1495.
20. Rathore, R.; Kochi, J. K. Tetrahedron Lett. 1994, 35, 8577.
21. Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3968.
22. For a preliminary account of a portion of this work, see: Seiders, J. R., II.; Wang, L.; Floreancig, P. E. J. Am. Chem. Soc. 2003, 125, 2406.
23. For other oxidative approaches to tetrahydropyran structures, see: (a) Yoshida, J.-i.; Ishichi, Y.; Isoc, S. J. Am. Chem. Soc. 1992, 114, 7594.
24. (b) Yoshida, J.-i.; Sugawara, M.; Kise, N. Tetrahedron Lett. 1996, 37, 3157.
25. (c) Chen, C.; Mariano, P. S. J. Org. Chem. 2000, 65, 3252.
26. Reference 3, p 85.
27. Wayner, D. D. M.; Sim, B. A.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 4853.
28. One volt is approximately 23 kcal/mol.
29. (a) Perrott. A. L.; de Lisjer, H. J. P.; Arnold, D. R. Can. J. Chem. 1997, 75, 384.
30. (b) Perrott, A. L.; Arnold, D. R. Can. J. Chem. 1992, 70, 272.
31. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375.
32. CAN that is used without purification provides variable results. We have found that a single purification provides a reagent that can be used for months without loss of activity. For the purification of CAN, see: Armarego, W. L. F.; Perrin, D. D. Purification of laboratory Chemicals, 4th ed.; Butterworth Heinemann: Oxford, U.K., 1996; p 376.
33. 3 or 0.97 V vs SCE. Zhang, Y.; Flowers, R. A., II. J. Org. Chem. 2003, 68, 4560.
34. A similar phenomenon was recently observed in oxidative oxocarbenium ion formation through carbon-hydrogen bond activation. Ying, B.-P.; Trogden, B. G.; Kohlman, D. T.; Liang, S. X.; Xu, Y.-C. Org. Lett. 2004, 6, 1523.
35. Hubig, S. M.; Rathore, R.; Kochi, J. K. J. Am. Chem. Soc. 1999, 121, 617.
36. Wong, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 5593.
37. For an excellent study of inner sphere electron transfer in metal-arene complexes, see: Lau, W.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 6720.
38. Kochi, J. K. Acc. Chem. Res. 1992, 25, 39.
39. Rollick, K. L.; Kochi, J. K. J. Am. Chem. Soc. 1982, 104, 1319.
40. Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567.
41. (a) Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915.
42. (b) Overman, L. E.; Castaneda, A.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 1303.
43. Cremer, D.; Gauss, J.; Childs, R. F.; Blackburn, C. J. Am. Chem. Soc. 1985, 107, 2435.
44. For examples, see: (a) D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1996, 79, 51.
45. (b) Tanaka, J.; Higa, T. Tetrahedron Lett. 1996, 37, 5535.
46. (c) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1996, 117, 8126.
47. This sequence can be considered as a cationic variant of the self-reproduction of chirality. See: Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
48. For lead references, see: (a) Bartlett, P. A.; Johnson, W. S.; Elliot, J. D. J. Am. Chem. Soc. 1983, 105, 2088.
49. (b) Denmark, S. E.; Wilson, T. M.; Almstead, N. G. J. Am. Chem. Soc. 1989, 111, 9258.
50. (c) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089.
51. (d) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6458.
52. (e) Denmark, S. E.; Almstead, N. G. J. Org. Chem. 1991, 56, 6485.
53. (f) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
54. Pinard, E.; Alanine, A.; Bourson, A.; Buettelmann, B.; Gill, R.; Hertz, M.-P.; Jaeschke, G.; Mutel, V.; Traube, G.; Wyler, R. Bioorg. Med. Chem. Lett. 2001, 11, 2173.
55. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
56. Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925.
57. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A. Synlett 1998, 26.
58. (a) Goosen, L. J.; Paetzold, J.; Koley, D. Chem. Commun. 2003, 706.
59. (b) Neveaux, M.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Perkin Trans. 1 1991, 1197.
60. Wayner, D. D. M.; Houman, A. Acta Chem. Scand. 1998, 52, 377.
61. Aldehyde 41 can be prepared on multigram scale through a two step sequence consisting of nucleophilic aromatic substitution of p-fluoroanisole by isobutyronitrile (Caron, S.; Vazquez, E.; Wojcik, J. M. J. Am. Chem. Soc. 2000, 122, 712) followed by DIBAL reduction.
62. For reagents that effect highly efficient and enantioselective additions into tertiary aldehydes, see: (a) Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920.
63. (b) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321.
64. (c) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
65. Inconsequential oxonia-Cope reactions might occur in these transformations. For examples of stereochemical erosion due to this process in related cyclization reactions, see: (a) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. D. Org. Lett. 2002, 4, 577.
66. (b) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815.
67. For total and formal syntheses of leucascandrolide A, see: (a) Hornberger, K. R.; Hamblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894.
68. (b) Fettes, A.; Carreira, E. M. Angew Chem. Int. Ed. 2002, 41, 4098.
69. (c) Wipf, P.; Reeves, J. T. Chem. Commun. 2002, 2006.
70. (d) Wang, Y.; Janjic, J.; Kozmin, S. A. J. Am. Chem. Soc. 2002, 124, 13670.
71. (e) Paterson, I.; Tudge, M. Angew. Chem., Int. Ed. 2003, 42, 343.
72. (f) Crimmins, M. T.; Siliphaivanh, P. Org. Lett. 2003, 5, 4641.
73. (g) Williams, D. R.; Plummer, S. V.; Patnaik, S. Angew. Chem., Int. Ed. 2003, 42, 3934.
74. The oxidation potentials of allylsilanes of this general structure can be estimated as being > 1.9 V vs SCE. See: Yoshida, J.-i.; Murata, T.; Isoe, S. Tetrahedron Lett. 1986, 27, 3373.
75. (a) Todd, W. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1991, 113, 3601.
76. (b) Ohga, K.; Yoon, U. C.; Mariano, J. P. J. Org. Chem. 1984, 49, 213.
77. Moeller, K. D.; Wang, P. O.; Tarazi, S.; Marzabadi, M. R.; Wong, P. L. J. Org. Chem. 1991, 56, 1058.