Intermolecular copper(I) chloride-mediated coupling of alkenyltrialkylstannane functions: A convenient synthesis of conjugated diene systems

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1173-1176

  Piers, Edward ^a   McEachern, Ernest J ^a   Romero, Miguel A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030058552     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02403-4     Document Type: Article

References (24)

1. Stille, J. K. Angew. Chem. Int. Ed. Eng. 1986, 25, 508.
2. Scott, W. J.; Crisp, G. T.; Stille, J. K. Org. Synth. 1990, 68, 116.
3. Mitchell, T. N. Synthesis 1992, 803.
4. Piers, E.; Wong, T. J. Org. Chem. 1993, 58, 3609.
5. Ghosal, S.; Luke, G. P.; Kyler, K. S. J. Org. Chem. 1987, 52, 4296.
6. Beddoes, R. L.; Cheeseright, T.; Wang, J.; Quayle, P. Tetrahedron Lett. 1995, 36, 283.
7. Interesting recent publications by Falck et al. and Takeda et al. should also be noted. The former group describe the copper(I) salt-mediated coupling of α-heteroatom-substituted alkyltributylstannane functions with a variety of electrophilic organohalides, while the latter researchers report the CuI-promoted allylation of alkenyltributylstannanes. See Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973 and Takeda, T.; Matsunaga, K.; Kabasawa, Y.; Fujiwara, T. Chem. Lett. 1995, 771.
8. Interesting recent publications by Falck et al. and Takeda et al. should also be noted. The former group describe the copper(I) salt-mediated coupling of α-heteroatom-substituted alkyltributylstannane functions with a variety of electrophilic organohalides, while the latter researchers report the CuI-promoted allylation of alkenyltributylstannanes. See Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973 and Takeda, T.; Matsunaga, K.; Kabasawa, Y.; Fujiwara, T. Chem. Lett. 1995, 771.
9. Piers, E.; Ellis, K. A. Tetrahedron Lett. 1993, 34, 1875.
10. Piers, E.; Gavai, A. V. J. Org. Chem. 1990, 55, 2374.
11. Piers, E.; Chong, J. M.; Gustafson, K.; Andersen, R. J. Can J. Chem. 1984, 62, 1.
12. Piers, E.; Wong, T.; Ellis, K. A. Can J. Chem. 1992, 70, 2058.
13. Piers, E.; Tse, H. L. A. Can J. Chem. 1993, 71, 983.
14. Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem. 1995, 60, 2322.
15. All new compounds reported herein displayed spectra in accord with structural assignments and gave satisfactory elemental (C, H) analyses and/or molecular mass determinations (high resolution MS).
16. Piers, E.; Morton, H. E.; Chong, J. M. Can J. Chem. 1987, 65, 78.
17. For a related transformation, see Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984, 25, 2415.
18. 2O, and the crude product was purified by flash chromatography on silica gel.
19. Houpis, I. N.; DiMichele, L.; Molina, A. Synlett. 1993, 365.
20. Negeshi, E.; Ay, M.; Gulevich, Y. V.; Noda, Y. Tetrahedron Lett. 1993, 34, 1437.
21. Wiessler, M. Tetrahedron Lett. 1977, 233.
22. Taylor, R. J. K. Synthesis 1977, 564.
23. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
24. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London. 1987.