An Efficient Synthesis of Conjugated Trienoic Acids via Stille Cross Coupling Reaction of (E)-1,2-Bis(tributylstannyl)ethylene

Synlett

Volumn 1997, Issue 7, 1997, Pages 771-772

  Thibonnet, Jérôme ^a   Abarbri, Mohamed ^a   Parrain, Jean Luc ^b   Duchêne, Alain ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003059547     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5746     Document Type: Article

References (25)

1. a) Vedejs, E.; Bershas, J.P. Tetrahedron Lett. 1975, 1359-1362 ;
2. b) Simpkins, N. "Sulphones in Organic Synthesis" Pergamon Press, Oxford 1993, p 254-284 ;
3. c) Kelly, S.E. "Alkene Synthesis" in Comprehensive Organic Synthesis, Trost, B.M. and Fleming, I. Ed. Pergamon, 1991, Oxford, vol.1 chap.3.
4. Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L.; Larchevêque, M. Synlett 1993, 217-218 and references therein.
5. Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
6. Pattenden, G.; Thom, S.M. Synlett 1993, 2883-2884.
7. Smith, A.B.; Ott, G.R. J. Am. Chem. Soc. 1996, 118, 13095-13096.
8. Le Menez, P.; Firmo, N.; Fargeas, V.; Ardisson, J.; Pancrazi, A. Tetrahedron 1996, 52, 6613-6618.
9. Macdonald, G.; Lewis, N.J.; Taylor, R.J.K. J. Chem. Soc., Chem. Commun. 1996, 2647-2648.
10. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
11. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
12. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
13. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
14. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
15. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
16. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
17. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
18. According to our knowledge, (E)-1,2-bis(tributylstannyl)ethylene has been generally used in the Stille approach for the synthesis of symmetrical bis coupling products, for examples see : a) Siesel, D.A.; Staley, S.W. Tetrahedron Lett. 1993, 23, 3679-3682 ; b) Galarini, R.; Musco, A.; Pontellini, R.; Bolognesi, A.; Destri, S.; J. Chem. Soc., Chem. Commun. 1991, 364-365 ; c) Zimmerman, E.K.; Stille, J.K. Macromolecules 1985, 18, 321-325. Only few publications described the sequential use of (E)-1,2-bis(tributylstannyl)ethylene for example see : d) Haak, R.A.; Penning, T.D.; Djuric, S.W.; Dziuba, J.A. Tetrahedron Lett. 1988, 29, 2783-2786 ; e) Naruse, Y.; Esaki, T., Yamamoto, H. Tetrahedron 1988, 44, 4747-4756 ; f) Djuric, S.W.; Haak, R.A.; Yu, S.S. J. Chem. Soc., Perkin Trans I 1989, 2133-2134; g) Barrett, A.G.M.; Edmunds, J.J.; Hendrix, J.A.; Horita, K.; Parkinson, C.J. J. Chem. Soc., Chem. Commun. 1992, 1238-1240 ; h) Mitchell, T.N. Synthesis 1992, 803-815 (footnote 72) ; i) Babudri, F.; Fiandanese, V.; Naso, F.; Punzi, A. Tetrahedron Lett. 1994, 35, 2067-2070.
19. a) Abarbri, M.; Parrain, J.L.; Duchêne, A. Tetrahedron Lett. 1995, 36, 2469-2472 ;
20. b) Abarbri, M.; Parrain, J.L.; Cintrat, J.C.; Duchêne, A. Synthesis 1996, 82-86.
21. Thibonnet, J.; Abarbri, M.; Parrain, J.L.; Duchêne, A. Tetrahedron Lett. 1996, 37, 7507-7510.
22. 2a-c are purified by column chromatography on reversed phase C18 silicagel.
23. Xiang, J.S.; Mahadevan, A.; Fuchs, P.L. J. Am. Chem. Soc. 1996, 118, 4284-4290.
24. a) Le Menez, P.; Firmo, N.; Fargeas, V.; Ardisson, J.; Pancrazi, A. Synlett 1994, 998-1000 ;
25. b) Under identical experimental conditions, reaction of (E)-1,2-bis(tributylstannyl)ethylene with the deconjugated isomer of 2a leads to 12% of the tributylstannyl transfer product.