Divalent Palladium Catalyzed Stereoselective Synthesis of α-(Z)-(Halomethylene)-γ-butyrolactone Derivatives and Its Mechanism

Journal of Organic Chemistry

Volumn 56, Issue 17, 1991, Pages 5120-5125

  Ma, Shengming ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001628288     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00017a025     Document Type: Article

References (64)

1. Zhang, Y.; O’Connor, B.; Negishi, E.-I. J. Org. Chem. 1988, 53, 5588.
2. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2033, 2049.
3. Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328.
4. Wu, G.; Lamaty, F.; Negishi, E.-I. J. Org. Chem. 1989, 54, 2507.
5. Oppolzer, W.; Gaudin, J.-M. Helv. Chim. Acta 1987, 70, 1477.
6. Oppolzèr, W.; Bedoya-Zurita, M.; Switzer, C. Y. Tetrahedron Lett. 1988, 29, 6433.
7. Oppolzer, W.; Swenson, R. E.; Gaudin, J.-M. Tetrahedron Lett. 1988, 29, 5529.
8. Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4149.
9. Piers, E.; Marais, P. C. Tetrahedron Lett. 1990, 55, 3454.
10. Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
11. Larock, R. C.; Hiu, C.-L.; Lau, H. H.; Varaprath, S. Tetrahedron Lett. 1984, 25, 4459.
12. O’Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
13. Negishi, E.-I.; Zhang, Y.; Shimoyama, I.; Wu, G. J. Am. Chem. Soc. 1989, 111, 8018.
14. Shimoyama, I.; Zhang, Y.; Wu, G.; Negishi, E.-I. Tetrahedron Lett. 1990, 31, 2841.
15. Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219.
16. Geng, L.; Lu, X. Tetrahedron Lett. 1990, 31, 111.
17. Trost, B. M.; Chen, S. J. Am. Chem. Soc. 1986, 108, 6053.
18. Bajan-Babu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128.
19. Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255.
20. Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651.
21. Yamamoto, A. Organotransition Metal Chemistry; John Wiley: New York, 1986; p 233.
22. Gammill, R. B.; Wilson, C. A.; Bryson, T. A. Synth. Commun. 1975, 5, 245.
23. Lee, K. H.; Huang, E.-S.; Piantodosi, C.; Pagani, J.; Geissman, T. A. Cancer Res. 1971, 31, 1649.
24. Grieco, P. A. Synthesis 1975, 67.
25. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. Synthesis. 1986, 157.
26. Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
27. Lee, E.; Ko, S. B.; Jung, K. W.; Chang, M. H. Tetrahedron Lett. 1989, 30, 827.
28. Haaima, G.; Weavers, R. T. Tetrahedron Lett. 1988, 29, 1085.
29. Bachi, M. D.; Bosch, E. Tetrahedron Lett. 1986, 27, 641.
30. Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630.
31. Henin, F.; Pete, J. P. Tetrahedron Lett. 1983, 24, 4687.
32. Jones, E. R. H.; Shen, T. Y.; Whiting, M. C. J. Chem. Soc. 1950, 230.
33. Clement, W. H.; Selwitz, C. M. J. Org. Chem. 1964, 29, 241.
34. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 2975.
35. Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 809.
36. Hosokawa, T.; Shimo, N.; Maeda, K.; Sonoda, A.; Murahashi, S.-I. Tetrahedron Lett. 1976, 383.
37. Jintoku, T.; Fujiwara, Y.; Kawata, I.; Kawauchi, T.; Taniguchi, H. J. Organomet. Chem. 1990, 385, 297.
38. Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranish, S. J. Org. Chem. 1979, 44, 56.
39. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
40. Minami, T.; Niki, I.; Agawa, T. J. Org. Chem. 1974, 39, 3236.
41. Tanaka, K.; Tamura, N.; Kaji, A. Chem. Lett. 1980, 596.
42. Ma, S.; Lu, X. Tetrahedron Lett. 1990, 31, 7653.
43. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 1643.
44. Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 2, p 150.
45. Wiger, G.; Albelo, G.; Rettig, M. F. J. Chem. Soc., Dalton Trans. 1974, 2242 and references cited therein.
46. Wipke, W. T.; Goeke, G. L. J. Am. Chem. Soc. 1974, 96, 4244.
47. Trost, B. M. Tetrahedron 1977, 33, 2615.
48. Hosokawa, T.; Montani, I.; Nishioka, S. Tetrahedron Lett. 1969, 3833.
49. Chatt, J.; Vallarino, L. M.; Venanzi, L. M. J. Chem. Soc. 1957, 3413.
50. Heπy, P. M. Acc. Chem. Res. 1973, 6, 16.
51. Doyle, J. R.; Slade, P. E.; Jonassen, H. B. Inorg. Synth. 1960, 6, 218.
52. Smith, E. F.; Wallace, D. L. J. Am. Chem. Soc. 1894, 16, 465.
53. Gramp, F. B. Ber. 1874, 7, 1723.
54. Uson, R.; Fornies, J.; Martinez, F. J. Organomet. Chem. 1977, 132, 429.
55. Stephenson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632.
56. Ukai, T.; Kawazura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.
57. Bahurel, Y.; Collonges, F.; Menet, A.; Pautet, F.; Poncet, A.; Descotes, G. Bull. Soc. Chim. Fr. 1971, 2203.
58. Mislow, K.; Hellman, H. M. J. Am. Chem. Soc. 1951, 73, 244.
59. Adams, R.; Adams, E. W. Organic Syntheses; Wiley; New York, 1941; Collect Vol. 1, p 459.
60. Allen, C. F. H.; Bell, A. Organic Syntheses; Wiley; New York, 1955; Collect Vol. 3, p 312.
61. Sweeting, O. J.; Johnson, J. R. J. Am. Chem. Soc. 1946, 68, 1057.
62. Heilbron, I.; Jones, E. R. H.; Sondheimer, F. J. Chem. Soc. 1949, 604.
63. Simmross, F.-M.; Weyerstahl, P. Synthesis 1981, 72.
64. Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier Amsterdam, 1988.