Water-mediated transition-metal-free Tsuji-Trost-type reaction

Tetrahedron Letters

Volumn 44, Issue 44, 2003, Pages 8099-8102

  Chevrin, Carole ^a   Le Bras, Jean ^a   Hénin, Françoise ^a   Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Allylic acetate; B AL1 SN1 mechanism; Palladium; Substitution; Water chemistry

Indexed keywords

1 ACETOXY 1,3 DIPHENYLPROPENE; ALKENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION; TSUJI TROST REACTION;

EID: 0141682457     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.038     Document Type: Article

References (32)

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14. For reviews, see: (a) Genêt, J.-P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317; (b) Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772; (c) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4094-4101; (d) Sinou, D. Adv. Synth. Catal. 2002, 344, 221-237.
15. For reviews, see: (a) Genêt, J.-P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317; (b) Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772; (c) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4094-4101; (d) Sinou, D. Adv. Synth. Catal. 2002, 344, 221-237.
16. For reviews, see: (a) Genêt, J.-P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317; (b) Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772; (c) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4094-4101; (d) Sinou, D. Adv. Synth. Catal. 2002, 344, 221-237.
17. For reviews, see: (a) Genêt, J.-P.; Savignac, M. J. Organomet. Chem. 1999, 576, 305-317; (b) Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772; (c) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4094-4101; (d) Sinou, D. Adv. Synth. Catal. 2002, 344, 221-237.
18. Deionized water was used in all experiments.
19. Commercial co-solvents were used as received.
20. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
21. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
22. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
23. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
24. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
25. 2R)CH(OAc)R′, but they involve Michael addition/elimination cascade reactions: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670; (b) Drewes, S. E.; Emslie, N. D.; Karodia, N.; Loizou, G. Synth. Commun. 1990, 20, 1437-1443; (c) Bauchat, P.; Le Rouillé, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267-271; (d) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron 2000, 56, 8133-8140; (e) Im, J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987-2990.
26. The substitution of 6-alkyl-4-cyclohexenyl substituted-benzoates by C-, N and S-nucleophiles has been reported in refluxing protic solvents: Magid, R. G. Tetrahedron 1980, 36, 1901-1930 and references cited therein.
27. The substitution of 6-alkyl-4-cyclohexenyl substituted-benzoates by C-, N and S-nucleophiles has been reported in refluxing protic solvents: Magid, R. G. Tetrahedron 1980, 36, 1901-1930 and references cited therein.
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30. (S)-1-Acetoxy-1,3-diphenylpropene, 92-99% e.e., was prepared from the corresponding enantio-enriched allylic alcohol obtained by stoichiometric kinetic resolution using Sharpless oxidation method: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240; (b) Roos, H. P.; Donovan, A. R. Tetrahedron: Asymmetry 1999, 10, 991-1000.
31. (S)-1-Acetoxy-1,3-diphenylpropene, 92-99% e.e., was prepared from the corresponding enantio-enriched allylic alcohol obtained by stoichiometric kinetic resolution using Sharpless oxidation method: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240; (b) Roos, H. P.; Donovan, A. R. Tetrahedron: Asymmetry 1999, 10, 991-1000.
32. (S)-1-Acetoxy-1,3-diphenylpropene, 92-99% e.e., was prepared from the corresponding enantio-enriched allylic alcohol obtained by stoichiometric kinetic resolution using Sharpless oxidation method: (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240; (b) Roos, H. P.; Donovan, A. R. Tetrahedron: Asymmetry 1999, 10, 991-1000.