A facile stereoselective synthesis of difunctionalized 1,3-dienes containing tin and halogen via hydrozirconation of (Z)-3-(tributylstannyl)alk-3-en-1-ynes

Journal of Organometallic Chemistry

Volumn 693, Issue 17, 2008, Pages 2954-2958

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

^a JIANGXI NORMAL UNIVERSITY   (China)

^b JIUJIANG UNIVERSITY   (China)

Author keywords

(E) Iodovinylstannane; Difunctionalized 1,3 diene; Hydrozirconation; Sonogashira coupling; Stereoselective synthesis

Indexed keywords

ACETYLENE; IODINE; LIGHTING; NONMETALS; STEREOCHEMISTRY; STEREOSELECTIVITY; TIN;

DESILYLATION; ELSEVIER (CO); HYDROZIRCONATION; SONOGASHIRA COUPLING; STEREO SELECTIVE SYNTHESIS; TRIMETHYLSILYL (TMS);

TITANIUM COMPOUNDS;

EID: 47749093873     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.06.002     Document Type: Short Survey

References (54)

1. Trost B.M., Vladuchick W.C., and Bridges A.J. J. Am. Chem. Soc. 102 (1980) 3554
2. Padwa A., and Norman B.H. Tetrahedron Lett. 29 (1988) 2417
3. Padwa A., Harrison B., Murphree S.S., and Yeske P.E. J. Org. Chem. 54 (1989) 4232
4. Yoshimatsu M., and Hasegawa J. J. Chem. Soc., Perkin Trans. 1 (1997) 211
5. Aversa M.C., Barattucci A., Bonaccorsi P., Giannetto P., and Jones D.N. J. Org. Chem. 62 (1997) 4376
6. Naso F. Pure Appl. Chem. 60 (1988) 79
7. Pearson W.H., Lin K.-C., and Poon Y.-F. J. Org. Chem. 54 (1989) 5814
8. Grieco P.A., May S.A., and Kaufman M.D. Tetrahedron Lett. 39 (1998) 7047
9. Cai M., Wang D., and Wang P. J. Organomet. Chem. 691 (2006) 737
10. Camasseto J.V., and Brandt C.A. Synthesis (1987) 146
11. Hevesi L., Hermans B., and Allard C. Tetrahedron Lett. 35 (1994) 6729
12. Zhu L.S., Huang Z.Z., and Huang X. Tetrahedron 52 (1996) 9819
13. Ma Y., and Huang X. J. Chem. Soc., Perkin Trans. 1 (1997) 2953
14. Negishi E., and Luo F.T. J. Org. Chem. 48 (1983) 1560
15. Luh T.-Y., and Wong K.-T. Synthesis (1993) 349
16. Ni Z.-J., Yang P.-F., Ng D.K.P., Tzeng Y.-L., and Luh T.-Y. J. Am. Chem. Soc. 112 (1990) 9356
17. Suzenet F., Blart E., and Quintard J.P. Synlett (1998) 879
18. Lipshutz B.H., and Lindsley C. J. Am. Chem. Soc. 119 (1997) 4555
19. Betzer J.F., Delaloge F., Muller B., and Pancrazi A. J. Org. Chem. 62 (1997) 7768
20. Backvall J.E., and Ericsson A. J. Org. Chem. 59 (1994) 5850
21. Back T.G., and Collins S. J. Org. Chem. 46 (1981) 3249
22. Chen Y., Evarts J.B., Torres E., and Fuchs P.L. Org. Lett. 4 (2002) 3571
23. Banert K., Fendel W., and Schlott J. Angew. Chem., Int. Ed. 37 (1998) 3289
24. Wang C., Song Q., and Xi Z. Tetrahedron 60 (2004) 5207
25. Banert K., and Schlott J. Tetrahedron 56 (2000) 5413
26. Herndon J.W., and Patel P.P. J. Org. Chem. 61 (1996) 4500
27. Desurmont G., Dalton S., Giolando D.M., and Srebnik M. J. Org. Chem. 61 (1996) 7943
28. Lipshutz B.H., and Lee J.I. Tetrahedron Lett. 32 (1991) 7211
29. Massaki S., Takuya K., and Tamejiro H. Synlett (2001) 1006
30. Li J.-H., Liang Y., and Xie Y.-X. J. Org. Chem. 69 (2004) 8125
31. Yoshimatsu M., and Hasegawa J. J. Chem. Soc., Perkin Trans. 1 (1997) 211
32. Huang X., and Xie M. Org. Lett. 4 (2002) 1331
33. Babudri F., Fiandanese V., Mazzone L., and Naso F. Tetrahedron Lett. 35 (1994) 8847
34. Su M., Kang Y., Yu W., Hua Z., and Jin Z. Org. Lett. 4 (2002) 691
35. Coleman R.S., and Walczak M.C. Org. Lett. 7 (2005) 2289
36. Cai M.-Z., Zhou Z., and Wang P.-P. Synthesis (2006) 789
37. Tsushima K., and Murai A. Tetrahedron Lett. 33 (1992) 4345 and references cited therein
38. Gao L.-X., and Murai A. Tetrahedron Lett. 33 (1992) 4349 and references cited therein
39. Maloney K.M., and Danheiser R.L. Org. Lett. 7 (2005) 3115 and references cited therein
40. Karle I.L. J. Am. Chem. Soc. 95 (1973) 4036
41. Inubushi Y., and Ibuka T. Heterocycles 17 (1982) 507
42. Stork G., and Zhao K. J. Am. Chem. Soc. 112 (1990) 5875
43. Hoshi M., Kawamura N., and Shirakawa K. Synthesis (2006) 1961
44. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
45. Sonogashira K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 3 (1991), Pergamon Press, Oxford 521-549 (Chapter 2.4, and references cited therein)
46. Schwartz J. J. Organomet. Chem. 1 (1976) 461
47. Hart D.W., Blackburn T.F., and Schwartz J. J. Am. Chem. Soc. 97 (1975) 679
48. Deloux L., and Srebnik M. J. Org. Chem. 59 (1994) 6871
49. Dabdoub M.J., and Baroni A.C.M. J. Org. Chem. 65 (2000) 54
50. Arefolov A., Langille N.F., and Panek J.S. Org. Lett. 3 (2001) 3281
51. Huang X., Duan D., and Zheng W. J. Org. Chem. 68 (2003) 1958
52. Fryzuk M.D., Bates G.S., and Stone C. J. Org. Chem. 56 (1991) 7201
53. Leusink A.J., Budding H.A., and Marsman J.W. J. Organomet. Chem. 9 (1967) 285
54. Lipshutz B.H., Keil R., and Barton J.C. Tetrahedron Lett. 33 (1992) 5861