Synthesis and hetero-Michael addition reactions of 2-alkynyl oxazoles and oxazolines

Organic and Biomolecular Chemistry

Volumn 3, Issue 1, 2005, Pages 31-35

  Wipf, Peter ^a   Graham, Thomas H ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; BIOSYNTHESIS; CARBON DIOXIDE; HALOGEN COMPOUNDS; ISOMERS; METABOLITES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY; TRANSITION METALS;

CONJUGATE ADDITION; CYCLIZATION; OXAZOLES; STEREOSELECTIVITY;

ADDITION REACTIONS;

DRUG DERIVATIVE; OXAZOLE DERIVATIVE; OXAZOLONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; OXAZOLES; OXAZOLONE; STEREOISOMERISM;

EID: 11844285621     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b413604g     Document Type: Article

References (77)

1. R. S. Roy, A. M. Gehring, J. C. Milne, P. J. Belshaw and C. T. Walsh, Nat. Prod. Rep., 1999, 16, 249.
2. (a) P. Wipf, Chem. Rev., 1995, 95, 2115;
3. (b) Z. Jin, Nat. Prod. Rep., 2003, 20, 584;
4. (c) Oxazoles: Synthesis, reactions, and spectroscopy, Part A, D. C. Palmer, ed., J. Wiley & Sons, Inc., Hoboken, NJ, 2003, vol. 60.
5. C. T. Walsh, ChemBioChem, 2002, 3, 124.
6. T. F. Molinski, Tetrahedron Lett., 1996, 37, 7879.
7. (a) R. Jansen, H. Irschik, H. Reichenbach, V. Wray and G. Höfle, Liebigs Ann. Chem., 1994, 759;
8. (b) H. Irschik, R. Jansen, K. Gerth, G. Höfle and H. Reichenbach, J. Antibiot., 1995, 48, 31;
9. (c) P. Wipf and T. H. Graham, J. Am. Chem. Soc., 2004, 126, 15346.
10. G. R. Delpierre, F. W. Eastwood, G. E. Gream, D. G. I. Kingston, P. S. Sarin, A. R. Todd and D. H. Williams, J. Chem. Soc. C, 1966, 1653.
11. J. W. Chamberlin and S. Chen, J. Antibiot., 1977, 30, 197.
12. G. I. Birnbaum and S. R. Hall, J. Am. Chem. Soc., 1976, 98, 1926.
13. (a) P. Wipf, Y. Aoyama and T. E. Benedum, Org. Lett., 2004, 6, 3593;
14. (b) L. Scarone, D. Sellanes, E. Manta, P. Wipf and G. Serra, Heterocycles, 2004, 63, 773;
15. (c) P. Wipf and J.-L. Methot, Org. Lett., 2001, 3, 1261;
16. (d) P. Wipf, C. P. Miller and C. M. Grant, Tetrahedron, 2000, 56, 9143.
17. To the best of our knowledge, this transformation has never been reported with oxazoles or oxazolines. However, HCl has been added to a 2-alkynyl thioazoline: R. C. Cambie, D. Chambers, P. S. Rutledge and P. D. Woodgate, J. Chem. Soc. Perkin Trans. 1, 1981, 40.
18. D. A. Evans, V. J. Cee, T. E. Smith and K. J. Santiago, Org. Lett., 1999, 1, 87.
19. A. R. Gangloff, B. Åkermark and P. Helquist, J. Org. Chem., 1992, 57, 4797.
20. P. Breuilles and D. Uguen, Tetrahedron Lett., 1998, 39, 3149.
21. D. R. Williams, M. P. Clark, U. Emde and M. A. Berliner, Org. Lett., 2000, 2, 3023.
22. Y. Nagao, S. Yamada and E. Fujita, Tetrahedron Lett., 1983, 24, 2287.
23. For an example of a nucleophilic addition to a non-enolizable β-carbonyl group, see: A. Yanagisawa, Y. Matsuzaki and H. Yamamoto, Synlett, 2001, 1855.
24. A. Nishida, M. Shibasaki and S. Ikegami, S. Chem Pharm. Bull., 1986, 34, 1434.
25. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
26. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
27. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
28. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
29. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
30. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
31. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
32. For examples of cyclization-oxidation sequences, see: (a) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (b) A. I. Meyers and F. X. Tavares, J. Org. Chem., 1996, 61, 8207; (c) F. Tavares and A. I. Meyers, Tetrahedron Lett., 1994, 35, 6803; (d) F. W. Eastwood, P. Perlmutter and Q. Yang, Tetrahedron Lett., 1994, 35, 2039; (e) J. C. Barrish, J. Singh, S. H. Spergel, W.-C. Han, T. P. Kissick, D. R. Kronenthal and R. H. Mueller, J. Org. Chem., 1993, 58, 4494; (f) F. Yokokawa, Y. Hamada and T. Shioiri, Synlett, 1992, 153; (g) C. Kashima and H. Arao, Synthesis, 1989, 873; (h) D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu and A. I. Meyers, J. Org. Chem., 1979, 44, 497.
33. For an oxidation-cyclization sequence, see: (a) P. Wipf and T. H. Graham, J. Org. Chem., 2001, 66, 3242; (b) P. Wipf and S. Lim, Chimia, 1996, 50, 157; (c) P. Wipf and S. Lim, J. Am. Chem. Soc., 1995, 117, 558; (d) P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604.
34. For an oxidation-cyclization sequence, see: (a) P. Wipf and T. H. Graham, J. Org. Chem., 2001, 66, 3242; (b) P. Wipf and S. Lim, Chimia, 1996, 50, 157; (c) P. Wipf and S. Lim, J. Am. Chem. Soc., 1995, 117, 558; (d) P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604.
35. For an oxidation-cyclization sequence, see: (a) P. Wipf and T. H. Graham, J. Org. Chem., 2001, 66, 3242; (b) P. Wipf and S. Lim, Chimia, 1996, 50, 157; (c) P. Wipf and S. Lim, J. Am. Chem. Soc., 1995, 117, 558; (d) P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604.
36. For an oxidation-cyclization sequence, see: (a) P. Wipf and T. H. Graham, J. Org. Chem., 2001, 66, 3242; (b) P. Wipf and S. Lim, Chimia, 1996, 50, 157; (c) P. Wipf and S. Lim, J. Am. Chem. Soc., 1995, 117, 558; (d) P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604.
37. (a) L. A. Dakin, N. F. Langille and J. S. Panek, J. Org. Chem., 2002, 67, 6812;
38. (b) K. J. Hodgetts and M. T. Kershaw, Org. Lett., 2002, 4, 2905;
39. (c) N. F. Langille, L. A. Dakin and J. S. Panek, Org. Lett., 2002, 4, 2485.
40. (a) Y. Wang, J. Janjic and S. A. Kozmin, J. Am. Chem. Soc., 2002, 124, 13670;
41. (b) R. D. Connell, F. Scavo, P. Helquist and B. Åkermark, Tetrahedron Lett., 1986, 27, 5559.
42. J. Coste, D. Le-Nguyen and B. Castro, Tetrahedron Lett., 1990, 31, 205.
43. While this work was in progress, Hoffmann and co-workers reported the synthesis of the ethyl ester of 9 by a different route: (a) I. V. Hartung, U. Eggert, L. O. Haustedt, B. Niess, P. M. Schäfer and H. M. R. Hoffmann, Synthesis, 2003, 1844; (b) L. O. Haustedt, S. B. Panicker, M. Kleinert, I. Y. Hartung, U. Eggert, B. Niess and H. M. R. Hoffmann, Tetrahedron, 2003, 59, 6967.
44. While this work was in progress, Hoffmann and co-workers reported the synthesis of the ethyl ester of 9 by a different route: (a) I. V. Hartung, U. Eggert, L. O. Haustedt, B. Niess, P. M. Schäfer and H. M. R. Hoffmann, Synthesis, 2003, 1844; (b) L. O. Haustedt, S. B. Panicker, M. Kleinert, I. Y. Hartung, U. Eggert, B. Niess and H. M. R. Hoffmann, Tetrahedron, 2003, 59, 6967.
45. In contrast, 2-vinyloxazole-4-carboxylic acid ethyl ester is reported to be unstable to storage: W. A. Donaldson and F. Ahmed, Synth. Commun., 2003, 33, 2685.
46. H. Kuroda, I. Tomita and T. Endo, Synth. Commun., 1996, 26, 1539.
47. J. Inanaga, Y. Baba and T. Hanamoto, Chem. Lett., 1993, 241.
48. S. Cossu, O. De Lucchi and R. Dürr, Synth. Commun., 1996, 26, 4597.
49. W. E. Truce and G. J. W. Tichenor, J. Org. Chem., 1972, 37, 2391.
50. Attempts to oxidize 2-(2-hydroxyethyl)oxazole-4-carboxylic acid methyl ester also resulted in decomposition:
51. (a) H. Tokuyama, S. Yokoshima, S.-C. Lin, L. Li and T. Fukuyama, Synthesis, 2002, 1121;
52. (b) T. Fukuyama, S.-C. Lin and L. Li, J. Am. Chem. Soc., 1990, 112, 7050.
53. B. M. Trost, T. N. Salzmann and K. Hiroi, J. Am. Chem. Soc., 1976, 98, 4887.
54. (a) V. K. Aggarwal and B. N. Esquivel-Zamora, J. Org. Chem., 2002, 67, 8618;
55. (b) V. K. Aggarwal, A. Thomas and S. Schade, Tetrahedron, 1997, 53, 16213;
56. (c) V. K. Aggarwal, A. Thomas and R. J. Franklin, J. Chem. Soc., Chem. Commun., 1994, 1653.
57. 2/C, see: Y. Mori and M. Seki, J. Org. Chem., 2003, 68, 1571.
58. For examples of enols that display intramolecular hydrogen bonding to nitrogen heterocycles, see: (a) L. W. Deady and T. Rodemann, J. Heterocycl. Chem., 2001, 38, 1185; (b) O. L. Acevedo, R. S. Andrews, M. Dunkel and P. D. Cook, J. Heterocycl. Chem., 1994, 31, 989.
59. For examples of enols that display intramolecular hydrogen bonding to nitrogen heterocycles, see: (a) L. W. Deady and T. Rodemann, J. Heterocycl. Chem., 2001, 38, 1185; (b) O. L. Acevedo, R. S. Andrews, M. Dunkel and P. D. Cook, J. Heterocycl. Chem., 1994, 31, 989.
60. E. J. Corey and B. W. Erickson, J. Org. Chem., 1971, 36, 3553.
61. 3, revealed strong chelation of thioether 10a to Ag(I) and Zn(II) salts. This scaffold may therefore be of broad utility in applications where rapid and straightforward access to metal-binding ligands is required. For a review of thioether ligands, see: A. M. Masdeu-Bultó, M. Diéguez, E. Martin and M. Gómez, Coord. Chem. Rev., 2003, 242, 159.
62. A. Pfaltz, Chimia, 2001, 55, 708.
63. P. Wipf and X. Wang, Org. Lett., 2002, 4, 1197.
64. A. Cevallos, R. Rios, A. Moyano, M. A. Pericås and A. Riera, Tetrahedron: Asymmetry, 2000, 11, 4407.
65. K. Bowden and M. J. Price, J. Chem. Soc. B, 1970, 1466.
66. M. Taniguchi, S. Kobayashi, M. Nakagawa, T. Hino and Y. Kishi, Tetrahedron Lett., 1986, 27, 4763.
67. (a) S. Ma and X. Lu, J. Chem. Soc. Chem. Commun., 1990, 1643;
68. (b) S. Ma and X. Lu, Tetrahedron Lett., 1990, 31, 7653;
69. (c) X. Lu, X. Huang and S. Ma, Tetrahedron Lett., 1992, 33, 2535;
70. (d) S. Ma, X. Lu and Z. Li, J. Org. Chem., 1992, 57, 709.
71. For additional studies of the hydrohalogenation of electron-deficient alkynes, see: (a) I. Marek, A. Alexakis and J.-F. Normant, Tetrahedron Lett., 1991, 32, 5329; (b) E. Piers, T. Wong, P. D. Coish and C. Rogers, Can. J. Chem., 1994, 72, 1816; (c) T. Zoller and D. Uguen, Tetrahedron Lett, 1998, 39, 6719; (d) R. Takeuchi, K. Tanabe and S. Tanaka, J. Org. Chem., 2000, 65, 1558.
72. For additional studies of the hydrohalogenation of electron-deficient alkynes, see: (a) I. Marek, A. Alexakis and J.-F. Normant, Tetrahedron Lett., 1991, 32, 5329; (b) E. Piers, T. Wong, P. D. Coish and C. Rogers, Can. J. Chem., 1994, 72, 1816; (c) T. Zoller and D. Uguen, Tetrahedron Lett, 1998, 39, 6719; (d) R. Takeuchi, K. Tanabe and S. Tanaka, J. Org. Chem., 2000, 65, 1558.
73. For additional studies of the hydrohalogenation of electron-deficient alkynes, see: (a) I. Marek, A. Alexakis and J.-F. Normant, Tetrahedron Lett., 1991, 32, 5329; (b) E. Piers, T. Wong, P. D. Coish and C. Rogers, Can. J. Chem., 1994, 72, 1816; (c) T. Zoller and D. Uguen, Tetrahedron Lett, 1998, 39, 6719; (d) R. Takeuchi, K. Tanabe and S. Tanaka, J. Org. Chem., 2000, 65, 1558.
74. For additional studies of the hydrohalogenation of electron-deficient alkynes, see: (a) I. Marek, A. Alexakis and J.-F. Normant, Tetrahedron Lett., 1991, 32, 5329; (b) E. Piers, T. Wong, P. D. Coish and C. Rogers, Can. J. Chem., 1994, 72, 1816; (c) T. Zoller and D. Uguen, Tetrahedron Lett, 1998, 39, 6719; (d) R. Takeuchi, K. Tanabe and S. Tanaka, J. Org. Chem., 2000, 65, 1558.
75. -1 less stable than (E)-10h.
76. See, for example: (a) S.-I. Murahashi, J. Organomet. Chem., 2002, 653, 27; (b) E. Negishi, J. Organomet. Chem., 2002, 653, 34.
77. See, for example: (a) S.-I. Murahashi, J. Organomet. Chem., 2002, 653, 27; (b) E. Negishi, J. Organomet. Chem., 2002, 653, 34.