Copper(I) chloride-mediated oxidative coupling of alkenyltrialkylstannyl functions: Efficient stereocontrolled syntheses of uniquely functionalized conjugated diene systems

Canadian Journal of Chemistry

Volumn 75, Issue 6, 1997, Pages 694-701

  Piers, Edward ^a   McEachern, Ernest J ^a   Romero, Miguel A ^a   Gladstone, Patricia L ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Alkenyltrialkylstannanes; Conjugated dienes; Copper(I) chloride; Organocopper; Organostannane; Oxidative coupling; Substituted dialkyl muconates; Transmetalation; trialkylstannyl ; unsaturated esters

Indexed keywords

CONFORMATIONS; COPPER; COPPER COMPOUNDS; ESTERS; ORGANIC SOLVENTS; OXIDATION; SYNTHESIS (CHEMICAL); TIN COMPOUNDS;

COUPLING REACTIONS; STEREOSELECTIVITY;

ORGANOMETALLICS;

EID: 0031169440     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-083     Document Type: Article

References (34)

1. J.K. Stille. Angew. Chem. Int. Ed. Engl. 25, 508 (1986).
2. W.J. Scott, G.T. Crisp, and J.K. Stille. Org. Synth. 68, 116 (1990).
3. T.N. Mitchell. Synthesis, 803 (1992).
4. L.S. Hegedus. In Organometallics in organic synthesis. Edited by M. Schlosser. Wiley, Chichester. 1994. pp. 413-417.
5. V. Farina. In Comprehensive organometallic chemistry II. Edited by E.W. Abel, E.G.A. Stone, and G. Wilkinson. Vol. 12. Edited by L.S. Hegedus. Elsevier, Oxford. 1995. pp. 200-220.
6. L.S. Liebeskind and R.W. Fengl. J. Org. Chem. 55, 5359 (1990).
7. C.R. Johnson, J.P. Adams, M.P. Braun, and C.B.W. Senanayake. Tetrahedron Lett. 33, 919 (1992).
8. L.S. Liebeskind and S.W. Rissinger. J. Org. Chem. 58, 408 (1993).
9. J. Ye, R.K. Bhatt, and J.R. Falck. J. Am. Chem. Soc. 116, 1 (1994).
10. G.P. Roth, V. Farina, L.S. Liebeskind, and E. Peña-Cabera. Tetrahedron Lett. 36, 2191 (1995).
11. V. Farina, S. Kapadia, B. Krishnan, C. Wang, and L.S. Liebeskind. J. Org. Chem. 59, 5905 (1994).
12. E. Piers and T. Wong. J. Org. Chem. 58, 3609 (1993).
13. G.D. Allred and L.S. Liebeskind. J. Am. Chem. Soc. 118, 2748 (1996).
14. E. Piers, E.J. McEachern, and M.A. Romero. Tetrahedron Lett. 37, 1173 (1996).
15. E. Piers and M.A. Romero. J. Am. Chem. Soc. 118, 1215 (1996).
16. S. Ghosal, G.P. Luke, and K.S. Kyler. J. Org. Chem. 52, 4296 (1987).
17. H.X. Zhang, F. Guibé, and G. Balavoine. J. Org. Chem. 55, 1857 (1990).
18. G.T. Crisp and P.T. Glink. Tetrahedron Lett. 32, 4649 (1992).
19. R.L. Beddoes, T. Cheeseright, J. Wang, and P. Quayle. Tetrahedron Lett. 36, 283 (1995).
20. J.R. Falck, R.K. Bhatt, and J. Ye. J. Am. Chem. Soc. 117, 5973 (1995).
21. T. Takeda, K. Matsunaga, Y. Kabasawa, and T. Fujiwara. Chem. Lett. 771 (1995).
22. E. Piers and K.A. Ellis. Tetrahedron Lett. 34, 1875 (1993).
23. E. Piers, T. Wong, and K.A. Ellis. Can. J. Chem. 70, 2058 (1992).
24. E. Piers, J.M. Chong, K. Gustafson, and R.J. Andersen. Can. J. Chem. 62, 1 (1984).
25. E. Piers and A.V. Gavai. J. Org. Chem. 55, 2374 (1990).
26. E. Piers and H.L.A. Tse. Can. J. Chem. 71, 983 (1993).
27. E. Piers, H.E. Morton, and J.M. Chong. Can. J. Chem. 65, 78 (1987).
28. I.N. Houpis, L. DiMichele, and A. Molina. Synlett, 365 (1993).
29. M. Wiessler. Tetrahedron Lett. 233 (1977).
30. R.J.K. Taylor. Synthesis, 564 (1977).
31. W.C. Still, M. Kahn, and A. Mitra. J. Org. Chem. 43, 2923 (1978).
32. E. Piers, E.J. McEachern, and P.A. Burns. J. Org. Chem. 60, 2322 (1995).
33. W.T. Elwell and D. Price. In Comprehensive analytical chemistry. Vol. 1C. Edited by C.L. Wilson and D.W. Wilson. Elsevier, Amsterdam. 1962. pp. 371-373.
34. M. Pereyre, J.-P. Quintard, and A. Rahm. Tin in organic synthesis. Butterworths, London. 1987.