Novel stereoselective synthesis of 1-substituted 1,3-dien-2-yl sulfides via Stille coupling reactions of (E)-α-stannylvinyl sulfides with alkenyl iodides

Journal of Organometallic Chemistry

Volumn 691, Issue 4, 2006, Pages 737-740

  Cai, Ming Zhong ^a   Wang, Dong ^a   Wang, Ping Ping ^b  

^a JIANGXI NORMAL UNIVERSITY   (China)

^b Jiujiang College   (China)

Author keywords

(E) stannylvinyl sulfide; 1,3 Dienyl sulfides; Difunctional reagent; Stereoselective synthesis; Stille coupling

Indexed keywords

METALLORGANIC CHEMICAL VAPOR DEPOSITION; OLEFINS; STEREOCHEMISTRY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

(E)-Α-STANNYLVINYL SULFIDE; 1,3-DIENYL SULFIDES; DIFUNCTIONAL REAGENTS; STEREOSELECTIVE SYNTHESIS; STILLE COUPLING;

ORGANOMETALLICS;

EID: 30844462315     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.10.012     Document Type: Article

References (42)

1. K. Mori The synthesis of insect pheromones J. ApSimon The Total Synthesis of Natural Products vol. 4 1981 Wiley New York
2. Y.Z. Huang, L. Shi, J. Yang, and J. Zhang Tetrahedron Lett. 28 1987 2159
3. W. Oppolzer Angew. Chem., Int. Ed. Engl. 23 1984 876
4. E. Arce, M.C. Carreno, M.B. Cid, and J.L.G. Ruano J. Org. Chem. 59 1994 3421
5. S. Ghosal, S.P. Luke, and K.S. Tyler J. Org. Chem. 52 1987 4296
6. R. Ideses, and A. Shani Tetrahedron 45 1989 3523
7. J.B. Baudin, G. Hareau, S.A. Julia, R. Lorne, and O. Ruel Bull. Soc. Chim. France 130 1993 856
8. E. Negishi, T. Takahashi, S. Baba, D.E. Van Horn, and N. Okukado J. Am. Chem. Soc. 109 1987 2393
9. K.S. Chan, and C.C. Mak Tetrahedron 50 1994 2003
10. A. Kasatkin, and R.J. Whitby J. Am. Chem. Soc. 121 1999 7039
11. T.Y. Luh, and K.T. Wong Synthesis 1993 349
12. E. Negishi, and F.T. Luo J. Org. Chem. 48 1983 1560
13. Z.J. Ni, P.F. Yang, D.K.P. Ng, Y.L. Tzeng, and T.Y. Luh J. Am. Chem. Soc. 112 1990 9356
14. M. Cai, W. Hao, H. Zhao, and C. Song J. Organomet. Chem. 679 2003 14
15. L. Hevesi, B. Hermans, and C. Allard Tetrahedron Lett. 35 1994 6729
16. L.S. Zhu, Z.Z. Huang, and X. Huang Tetrahedron 52 1996 9819
17. Y. Ma, and X. Huang J. Chem. Soc., Perkin Trans. 1 1997 2953
18. F. Suzenet, E. Blart, and J.P. Quintard Synlett 1998 879
19. B.H. Lipshutz, and C. Lindsley J. Am. Chem. Soc. 119 1997 4555
20. J.F. Betzer, F. Delaloge, B. Muller, and A. Pancrazi J. Org. Chem. 62 1997 7768
21. M. Cai, H. Ye, H. Zhao, and C. Song J. Organomet. Chem. 687 2003 462
22. T.Y. Luh, and Z.J. Ni Synthesis 1990 89
23. K.D. Gundermann, and P. Holtmann Angew. Chem., Int. Ed. Engl. 5 1966 668
24. B.M. Trost, and A.V. Lavoie J. Am. Chem. Soc. 105 1983 5057
25. T.H. Chan, and C.V.C. Prasad J. Org. Chem. 52 1987 110
26. P.G. McDougal, Y.-I. Oh, and D. VanDerveer J. Org. Chem. 54 1989 91
27. L.E. Overman, C.B. Petty, T. Ban, and G.T. Huang J. Am. Chem. Soc. 105 1983 6335
28. W.H. Pearson, K.-C. Lin, and Y.-F. Poon J. Org. Chem. 54 1989 5814
29. P.A. Grieco, S.A. May, and M.D. Kaufman Tetrahedron Lett. 39 1998 7047
30. F. Naso Pure Appl. Chem. 60 1988 79
31. R.J. Pariza, and P.L. Fuchs J. Org. Chem. 50 1985 4252
32. S.-S.P. Chou, S.-Y. Liou, C.-Y. Tsai, and A.-J. Wang J. Org. Chem. 52 1987 4468
33. Y. Ikeda, K. Furuta, N. Meguriya, N. Ikeda, and H. Yamamoto J. Am. Chem. Soc. 104 1982 7663
34. A. Tsirk, S. Gronowitz, and A.-B. Hörnfeldt Tetrahedron 54 1998 9529
35. G.D. Allred, and L.S. Liebeskind J. Am. Chem. Soc. 118 1996 2748
36. M. Su, Y. Kang, W. Yu, Z. Hua, and Z. Jin Org. Lett. 4 2002 691
37. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
38. D. Gschneidner J. Am. Chem. Soc. 115 1993 6625
39. V. Farina Pure Appl. Chem. 68 1996 73
40. T.N. Mitchell Synthesis 1992 803
41. J.K. Stille, and B.L. Groh J. Am. Chem. Soc. 109 1987 813
42. P.A. Magriotis, J.T. Brown, and M.E. Scott Tetrahedron Lett. 32 1991 5047