An efficient synthesis of stereodefined enynes and dienes via Pd-catalyzed reaction of chloroenynes and chlorodienes with Grignard reagents

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2447-2450

  Ramiandrasoa, Parfait ^a   Bréhon, Bernard ^b   Thivet, Armelle ^a   Alami, Mouâd ^a,b   Cahiez, Gérard ^a  

^a Ecl Sup Chim Organique Minerale   (France)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Chlorodienes; Chloroenynes; Dienes; Dienynes; Enynes; Palladium; Trienes

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0343471429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00365-1     Document Type: Article

References (22)

1. (a) Heck, R.F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
2. (b) Kalinin, V.N. Synthesis 1992, 413-432 and references cited therein.
3. (a) Tamao, K. in Comprehensive Organic Synthesis, Vol. 3; Trost, B.M.; Fleming, I.; Pattenden, G. Ed.; Pergamon Press: Oxford, 1991, pp 435-480.
4. (b) Knight, D.W. in Comprehensive Organic Synthesis, Vol. 3; Trost, B.M.; Fleming, I.; Pattenden, G. Ed.; Pergamon Press: Oxford, 1991, pp 481-520.
5. For the coupling of vinyl chlorides with Grignard reagents under palladium catalysis see: (a) Ratovelomanana, V.; Linstrumelle, G. Synth. Comm. 1984, 14, 179-187.
6. (b) Hoffmann, R.W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem. 1993, 629-639.
7. (c) Sugihara, Y.; Ogasawara, K. Synlett 1994, 665-666.
8. For the coupling of polychloroolefins see: (d) Linstrumelle, G.; Alami, M. (E) and (Z)-dichloroethylene in Encyclopedia of Reagents for Organic Synthesis, Paquette, L., Ed., Wiley, Chichester, 1995, 3, 1710-1712.
9. (e) Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1981, 22, 315-318.
10. (f) Ratovelomanana, V.; Linstrumelle, G.; Normant, J.F. Tetrahedron Lett. 1985, 26, 2575-2576.
11. The coupling of vinyl chlorides with Grignard reagents under nickel catalysis has been described see: (a) Corriu, R.J.P.; Masse, J.P. J. Chem. Soc. Chem. Comm. 1972, 144.
12. (b) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.I.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Soc. Chim. Jpn. 1976, 49, 1958-1969.
13. (c) Hosoni, A.; Saito, M.; Sakurai, H. Tetrahedron Lett. 1979, 429-432.
14. (d) Babudri, F.; Fiandanese, V.; Mazzone, L.; Naso, F. Tetrahedron Lett. 1994, 35, 8847-8850
15. For the coupling under iron catalysis see: (e) Cahiez, G.; Marquais, S. Tetrahedron Lett. 1996, 37, 1773-1776.
16. Alami M., Linstrumelle G. Tetrahedron Lett. 32:1991;6109-6112.
17. (a) Chemin, D.; Linstrumelle, G. Tetrahedron 1994, 50, 5335-5344.
18. (b) Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209-1220.
19. (a) Jones, E.R.H.; Thallez, V.; The Chemistry of Carbon-Carbon Triple Bond, part II; Patai, S., Interscience, New York, 1978, pp 621.
20. (b) Bohlmann, F.; Burkhardt, T.; Zdero, C. Naturally Occurring Acetylenes, Academic Press, New York, 1973.
21. 3) δ 139.95, 136.55, 128.60, 128.20, 126.00, 108.90, 93.10, 79.70, 31.15, 28.50, 22.25, 19.65, 14.00.
22. 2(dppf) is described to depress side reactions particularly β-elimination see: Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.