Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1958-1963

  Huang, Xian ^a,b   Duan, Dehui ^a,b   Zheng, Weixin ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONATION; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

HYDROZIRCONATION;

KETONES;

FUNCTIONAL GROUP; KETONE; SULFONE DERIVATIVE; SULFOXIDE; TETRAHYDROFURAN; VINYL DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037424324     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0111154     Document Type: Article

References (48)

1. (a) Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115.
2. (b) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
3. For a recent review on alkenylzirconocene, see: Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
4. (a) Dabdo2.ub, M. J.; Baroni, A. C. M. J. Org. Chem. 2000, 65, 54.
5. (b) Sung, J. W.; Jang, W. B.; Oh, D. Y. Tetrahedron Lett. 1996, 37, 7537.
6. (c) Huang, X.; Wang, J.-H.; Yang, D.-Y. J. Chem. Soc., Perkin Trans. 1 1999, 673.
7. (a) Liu, L. K.; Chi, Y.; Jen, K. Y. J. Org. Chem. 1980, 45, 406.
8. (b) Back, T. G.; Collins, S. J. Org. Chem. 1981, 46, 3249.
9. (c) Happer, D. A. R.; Steenson, B. E. Synthesis 1980, 806.
10. (d) Posner, G. H.; Brunelle, D. J. J. Org. Chem. 1972, 37, 3547.
11. (a) Mikolajczyk, M.; Perlikowska, W.; Omelanczuk, J.; Cristau, H. J.; Perraud-Darcy, A. J. Org. Chem. 1998, 63, 9716.
12. (b) Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078.
13. (c) Posner, G. H.; Tang, P. W. J. Org. Chem. 1978, 43, 4131.
14. (a) De Lucchi, O.; Pasquato, L. Tetrahedron 1988, 44, 6755.
15. (b) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
16. (c) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903.
17. (d) Carreno, M. C. Chem. Rev. 1995, 95, 1717.
18. Huang, X.; Duan, D. H. J. Chem. Soc., Chem. Commun. 1999, 1741.
19. Mikolajczyk, M.; Midura, W. H.; Grzejszczak, S.; Zatorski, A.; Chefczynska, A. J. Org. Chem. 1978, 43, 473.
20. Ma, S. M.; Lu, X. Y.; Li, Z. G. J. Org. Chem. 1992, 57, 709.
21. Russel, G. A.; Ochrymowycz, L. A. J. Org. Chem. 1970, 35, 2106.
22. Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317.
23. (a) Cardillo, G.; Savoia, D.; Umani-Ronchi, A. Synthesis 1975, 453.
24. (b) Bentani, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1 1995, 1035.
25. (a) Yoshimatsu, M.; Hayashi, M.; Tanabe, G.; Muraoka, O. Tetrahedron Lett. 1996, 37, 4161.
26. (b) Yoshimatsu, M.; Hasegawa, J. Tetrahedron Lett. 1996, 37, 7381.
27. Hohmann, M.; Krause, N. Chem. Ber. 1995, 128, 851.
28. Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727.
29. Hara, R.; Liu, Y.; Sun, W.-H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4103.
30. Haynes, R. K.; Vonwiller, S. C.; Stokes, J. P.; Merlino, L. M. Aust. J. Chem. 1988, 41, 881.
31. Najera, C.; Baldo, B.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1988, 1029.
32. Wipf, P.; Xu, W. Synlett 1992, 718.
33. CCDC no. 188257.
34. CCDC no. 188258.
35. (a) Ma, S. M.; Negishi, E. I. J. Org. Chem. 1997, 62, 784.
36. (b) Ma, S.; Wei, Q.; Wang, H. Org. Lett. 2000, 2, 3893.
37. Whitmore, F. C.; Hamilton, F. H. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. 1, p 492.
38. Rao, M. L. N.; Periasamy, M. Synth. Commun. 1995, 25, 2295.
39. Cacchi, S.; Caglioti, L.; Zappelli, P.J. Org. Chem. 1973, 38, 3653.
40. Buchwald, S. L.; Lamaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
41. Suzuki, H.; Abe, H. Tetrahedron Lett, 1996, 37, 3717.
42. Jang, W. B.; Jeon, H. J.; Oh, D. Y. Synth. Commun. 1998, 28, 1253.
43. Srinivasan, C.; Granesan, P. K.; Arumugam, N. Indan J. Chem. 1983, 22B, 649.
44. Matano, Y.; Yoshimune, M. Azuma, N.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1996, 1971.
45. Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821.
46. (a) Amiel, Y. J. Org. Chem. 1974, 39, 3867.
47. (b) Amiel, Y. J. Org. Chem. 1971, 36, 3691.
48. (c) Amiel, Y. J. Org. Chem. 1971, 36, 3697.