Allylidenetriphenylphosphorane as a Bifunctional Reagent: Synthesis of Cyclopentenones and α,β-Unsaturated Ketones with [3-(Alkoxycarbonyl)-2-ethoxy-2-propenylidene]triphenylphosphorane

Journal of Organic Chemistry

Volumn 59, Issue 1, 1994, Pages 111-119

  Hatanaka, Minoru ^a   Himeda, Yuichiro ^a   Imashiro, Ritsuo ^a   Tanaka, Yasuhiro ^a   Ueda, Ikuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0028354822     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00080a019     Document Type: Article

References (57)

1. Maercker, A. Org. React. 1965, 14, 289
2. Johnson, A. W. In Ylid Chemistry; Academic Press: New York, 1966
3. Gedye, R. N.; Westaway, D. C.; Arora, P.; Bisson, R.; Khalil, A. H. Can. J. Chem. 1977, 55, 1218
4. Toshima, K.; Tatsuta, K.; Kinoshita, M. Tetrahedron Lett. 1986, 27, 4741
5. Roush, W. R.; Coe, J. W. Tetrahedron Lett. 1987, 28, 931
6. Shistido, Y.; Kitabayashi, C. J. Org. Chem. 1992, 57, 2876
7. Lavielle, G. C. R. Acad. Sci. 1970, 270, 86
8. Vedejs, E.; Bershas, J P.; Fuchs, L. F. J. Org. Chem. 1973, 38, 3625
9. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1974, 39, 821
10. Stingier, A. H.; Weir, N. G. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Elks, J., Ed.; Chem. Soc. Special Publication No. 28; Chemical Society: London, 1977; p 153
11. Bestmann, H. J. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p 171
12. Bestmann, H.J.; Zimmermann, R. In Methoden der Organishen Chemie; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; Vol. E1, p 616
13. Zbiral, E.; Berner-Fenz, L. Tetrahedron 1968, 24, 1363
14. Issleib, K.; Lieschewski, M. J. Prakt. Chem. 1969, 311, 857
15. Vedeja, E.; Bershas, J. P. Tetrahedron Lett. 1975, 1359
16. Bestmann, H. J.; Roth, K. Angew. Chem., Int. Ed. Engl. 1981, 20, 575
17. Bogdanovic, B.; Konstantinovic, S. Synthesis 1972, 481
18. Büchi, G.; Wüest, H. Helv. Chim. Acta. 1971, 54, 1767
19. Bohlmann, F.; Zdero, C. Chem. Ber. 1973, 106, 3779
20. Dauben, W. G.; Ipaktscti, J. J. Am. Chem. Soc. 1973, 95, 5088
21. Dauben, W. G.; Hart, D. J.; Ipaktscti, J.; Kozikowski, A. P. Tetrahedron Lett. 1973, 4425
22. Padwa, A.; Brodsky, L. J. Org. Chem. 1974, 39, 1318
23. Vedejs, E.; Bershas, J. P. Tetrahedron Lett. 1975, 1359
24. Martin, S. F.; Desai, S. R. J. Org. Chem. 1977, 42, 1664
25. Hatanaka, M.; Yamamoto, Y.; Ishimaru, T. J. Chem. Soc., Chem. Commun. 1984, 1705
26. Hatanaka, M.; Himeda, Y.; Ueda, I. J. Chem. Soc., Chem. Commun. 1990, 526
27. Ramaiah, M. Synthesis 1984, 529
28. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1
29. Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Eds.; Pergamon: Oxford, 1991, Vol. 6, p 1037
30. Curran, D. P. Synthesis 1988, 417, 489
31. Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J.-B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438
32. Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788
33. Beak, P.; Burg, D. A. J. Org. Chem. 1989, 54, 1647
34. Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286
35. Buchwald, S. L.; Lum, R. T.; Fisher, R. A.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 9113
36. Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336
37. Hirst, G. C.; Howard, P. N.; Overman, L. E. J. Am. Chem. Soc. 1989, 111, 1614
38. Mathau, J. J. Chem. Soc., Chem. Common. 1990, 1264
39. Ejiri, S.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. (1999)
40. Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4621
41. Hatanaka, M.; Imashiro, R.; Ueda, I. Chem. Lett. 1992, 2253
42. Howe, R. K. J. Am. Chem. Soc. 1971, 93, 3457
43. McLean, S.; Hynes, P. Tetrahedron 1965, 21, 2313, 2343
44. Bestmann, H.-J.; Haberlein, H.; Pils, I. Tetrahedron 1964, 20, 2079
45. Bestmann, H.-J.; Seng, F.; Shulz, H. Chem. Ber. 1963, 96, 465
46. Wiley, R. H.; Crawford, T. H.; Staples, C. S. J. Chem. Soc. 1962, 1535
47. Huet, F.; Lechevallier, A.; Pallet, M.; Conia, J. M. Synthesis 1978, 63
48. Krapcho, A. P. Synthesis 1982, 805, 893
49. Nomura, H. J. Chem. Soc. 1917, 769
50. Nomura, H. Sci. Rep. Tohoku Imp. Univ. 1918, 7, 67
51. Nomura, H. Sci. Rep. Tohoku Imp. Univ 1925, 14, 131.
52. Connell, D. W.; Sutherland, M. D. Aust. J. Chem. 1969 22 1033
53. Kochhar, K. S.; Pinnich, H. W. J. Org. Chem. 1984, 49, 3222.
54. Brynes, S. D.; Feder, L. R. J. Am. Chem. Soc. 1972, 94, 7016
55. Hellow, J.; Kingston, J. F.; Fallis, A. G. Synthesis 1984, 1014
56. Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1987, 28, 175
57. Liotta, D.; Zima, G.; Saindane, M. J. Org. Chem. 1982, 47, 1258