Rhodium-catalyzed heterocycloaddition of a diazomalonate and a nitrile: 4-Carbomethoxy-5-methoxy-2-phenyl-1,3-oxazole

Organic Syntheses

Volumn 74, Issue , 1997, Pages 229-

  Tullis, Joshua S ^b   Helquist, Paul ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026882818     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.074.0229     Document Type: Article

References (63)

1. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709–1716.
2. Wulfman, D. S.; Yousefian, S.; White, J. M. Synth. Commun. 1988, 18, 2349–2352;
3. Wulfman, D. S.; Roberts, J.; Henderson, D. K.; Romine, J. C.; McDaniel, R. S., Jr.; Carver, L.; Beistel, D. W. Can. J. Chem. 1984, 62, 554–560;
4. Ciganek, E. J. Org. Chem. 1965, 30, 4366–4367.
5. Connell, R. D. Ph.D. Dissertation, University of Notre Dame, 1989.
6. (a) Lewis, J. R. Natural Product Reports 1995, 12, 135–64;
7. Hassner, A.; Fischer, B. Heterocycles, 1993, 35, 1441–65;
8. Pattenden, G. J. Heterocycl. Chem. 1992, 29, 607–618;
9. "Oxazoles"; Turchi, I. J., Ed.; Wiley: New York, 1986.
10. Doyle, K. J.; Moody, C. J. Tetrahedron 1994, 50, 3761–3772;
11. Wasserman, H. H.; McCarthy, K. E.; Prowse, K. S. Chem. Rev. 1986, 86, 845–856.
12. Videnov, G.; Kaiser, D.; Kempter, C.; Jung. G. Angew. Chem. Int. Ed. Engl. 1996, 35(13/14), 1503–1506;
13. Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66(10/11), 2107–2110;
14. Helquist, P.; Bergdahl, M.; Hett. R.; Gangloff, A. R.; Demillequand, M.; Cottard, M.; Mader, M. M.; Friebe, T.; Iqbal, J.; Wu, Y.; Åkermark, B.; Rein, T.; Kann, N. Pure Appl. Chem. 1994, 66 (10/11), 2063–2066;
15. Jacobi, P. A., "Bis-Heteroannulation: Total Synthesis of Furanoterpenes, Butenolides, Lactones and Related Materials", In Adv. in Heterocycl. Nat. Prod. Synth. 1992, 2, 215–298;
16. (b) Subramanyam, C.; Noguchi, M.; Weinreb, S. M. J. Org. Chem. 1989, 54, 5580–5585.
17. Cocito, C. Antibiotics (N.Y.) 1983, 6, 296–332;
18. Di Giambattista, M.; Chinali, G.; Cocito, C. J. Antimicrob. Chemother. 1989, 24, 485–507;
19. Paris, J. M.; Barrière, J. C.; Smith, C.; Bost, P. E. Recent Prog. Chem. Synth. Antibiot.; Lukacs, G.; Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; Vol. 1, pp 183–248.
20. (a) Meyers, A. I.; Lawson, J. P.; Walker, D. G.; Linderman, R. J. J. Org. Chem. 1986, 51, 5111–5123;
21. Nagao, Y.; Yamada, S.; Fujita, E. Tetrahedron Lett. 1983, 24, 2287–2290, 2291–2294;
22. Wood, R. D.; Ganem, B. Tetrahedron Lett. 1983, 24, 4391–4392;
23. Yokoyama, M.; Menjo, Y.; Ubukata, M.; Irie, M.; Watanabe, M.; Togo, H. Bull. Chem. Soc. Jpn. 1994, 67, 2219–2226;
24. Tavares, F.; Lawson, J. P.; Meyers, A. I. J. Am. Chem. Soc. 1996, 118, 3303–3304.
25. (e) Lipshutz, B. H.; Hungate, R. W. J. Org. Chem. 1981, 46, 1410–1413.
26. (a) Dow, R. L. J. Org. Chem. 1990, 55, 386–388;
27. Zhao, Z.; Scarlato, G. R.; Armstrong, R. W. Tetrahedron Lett. 1991, 32, 1609–1612;
28. Smith, A. B., III; Salvatore, B. A.; Hull, K. G.; Duan, J. J.-W. Tetrahedron Lett. 1991, 32, 4859–4862;
29. Yokoyama, M.; Sujino, K.; Irie, M.; Togo, H. Tetrahedron Lett. 1991, 32, 7269–7272;
30. Yokoyama, M.; Irie, M.; Sujino, K.; Kagemoto, T.; Togo, H.; Funabashi, M. J. Chem. Soc., Perkin Trans. I 1992, 2127–2134;
31. Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961–1963;
32. Cunico, R. F.; Kuan, C. P. J. Org. Chem. 1992, 57, 3331–3336;
33. Yokokawa, F.; Hamada, Y.; Shioiri, T. SynLett 1992, 153–155;
34. Williams, E. L. Tetrahedron Lett. 1992, 33, 1033–1036;
35. Doyle, K. J.; Moody, C. J. Tetrahedron Lett. 1992, 33, 7769–7770;
36. Eissenstat, M. A.; Weaver, J. D., III J. Org. Chem. 1993, 58, 3387–3390;
37. Kawase, M.; Miyamae, H.; Narita, M.; Kurihara, T. Tetrahedron Lett. 1993, 34, 859–862;
38. Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449–8450;
39. Shapiro, R. J. Org. Chem. 1993, 58, 5759–5764;
40. Parsons, R. L., Jr.; Heathcock, C. H. J. Org. Chem. 1994, 59, 4733–4734;
41. Eastwood, F. W.; Perlmutter, P.; Yang, Q. Tetrahedron Lett. 1994, 35, 2039–2042;
42. Meyers, A. I.; Tavares, F. Tetrahedron Lett. 1994, 35, 2481–2484;
43. Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558–559;
44. Patonay, T.; Hoffman, R. V. J. Org. Chem. 1995, 60, 2368–2377;
45. Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623–4633.
46. Cornforth, J. W.; Cornforth, R. H. J. Chem. Soc. 1947, 96–102.
47. (a) Buu, N. T.; Edward, J. T. Can. J. Chem. 1972, 50, 3730–3737;
48. Moniotte, Ph. G.; Hubert, A. J.; Teyssié, Ph. J. Organomet. Chem. 1975, 88, 115–120;
49. Ibata, T.; Sato, R. Chem. Lett. 1978, 1129–1130;
50. Ibata, T.; Sato, R. Bull. Chem. Soc. Jpn. 1979, 52, 3597–3600;
51. Doyle, M. P.; Buhro, W. E.; Davidson, J. G.; Elliott, R. C.; Hoekstra, J. W.; Oppenhuizen, M. J. Org. Chem. 1980, 45, 3657–3664;
52. Mashraqui, S. H.; Keehn, P. M. J. Am. Chem. Soc. 1982, 104, 4461–4465;
53. Nagayoshi, K.; Sato, T. Chem. Lett. 1983, 1355–1356;
54. Ibata, T.; Isogami, Y. Bull. Chem. Soc. Jpn. 1989, 62, 618–620;
55. Vedejs, E.; Piotrowski, D. W. J. Org. Chem. 1993, 58, 1341–1348.
56. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49–92;
57. Ye, T.; McKervey Chem. Rev. 1994, 94, 1091–1160;
58. Doyle, M. P. Chem. Rev. 1986, 86, 919–939;
59. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765–1808.
60. Huisgen, R. In "1,3-Dipolar Cycloaddition Chemistry"; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, Chap. 1, pp 1–176;
61. "Advances in Cycloaddition"; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1988; Vol. 1;
62. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263–309.
63. Connell, R. D.; Tebbe, M.; Gangloff, A. R.; Helquist, P.; Åkermark, B. Tetrahedron 1993, 49, 5445–5459.