Palladium-Catalyzed Synthesis of Stereodefined 4-Arylidene-3 Tosyloxazolidin-2-ones from 2-Propynyl Tosylcarbamates and Unsaturated Halides (or Triflate)

Synlett

Volumn 1997, Issue 8, 1997, Pages 944-946

  Bouyssi, Didier ^a   Cavicchioli, Marcello ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

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Indexed keywords

EID: 1542782481     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-935     Document Type: Article

References (35)

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2. a) stabilized enolates as nucleophiles onto a carbon-carbon double bond : Bouyssi, D.; Balme, G.; Fournet, G.; Monteiro, N.; Gore, J. Tetrahedron Lett. 1991, 32, 1641. Bruyère, D.; Gaignard, G.; Bouyssi, D.; Balme, G.; Lancelin, J. M. Tetrahedron Letters, 1997, 38, 827 and references therein.
3. a) stabilized enolates as nucleophiles onto a carbon-carbon double bond : Bouyssi, D.; Balme, G.; Fournet, G.; Monteiro, N.; Gore, J. Tetrahedron Lett. 1991, 32, 1641. Bruyère, D.; Gaignard, G.; Bouyssi, D.; Balme, G.; Lancelin, J. M. Tetrahedron Letters, 1997, 38, 827 and references therein.
4. b) stabilized enolates as nucleophiles onto a carbon-carbon triple bond: Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1991, 47, 6293.
5. (c) carboxylates as nucleophiles : Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett., 1992, 33, 2811. Bouyssi, D. ; Goré, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett., 1993, 34. 3129. Cavicchioli , M.; Bouyssi , D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429. Cavicchioli , M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52 , 11463.
6. (c) carboxylates as nucleophiles : Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett., 1992, 33, 2811. Bouyssi, D. ; Goré, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett., 1993, 34. 3129. Cavicchioli , M.; Bouyssi , D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429. Cavicchioli , M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52 , 11463.
7. (c) carboxylates as nucleophiles : Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett., 1992, 33, 2811. Bouyssi, D. ; Goré, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett., 1993, 34. 3129. Cavicchioli , M.; Bouyssi , D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429. Cavicchioli , M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52 , 11463.
8. (c) carboxylates as nucleophiles : Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett., 1992, 33, 2811. Bouyssi, D. ; Goré, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett., 1993, 34. 3129. Cavicchioli , M.; Bouyssi , D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429. Cavicchioli , M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52 , 11463.
9. (a) Inoue, Y.; Itom, Y.; Yen, J.F.; Imaizumi, S. J.Mol. Catal., 1990, 60, L1-L3.
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11. (c) Luo, F.T.; Schreuder, I.; Wang, R.J. J.Org.Chem. 1992, 57, 2213 .
12. (d) Luo, F.T.; Wang, R.T. Tetrahedron Lett., 1992, 33, 6835.
13. (e) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F.; Tetrahedron 1994, 50, 437.
14. (f) Saulnier, M.G.; Frenesson, D.B.; Deshpande, M.S.; Vyas, D.M. Tetrahedron Lett. 1995, 36, 7841.
15. (g) Arcadi, A. ; Rossi, E. Tetrahedron Lett. 1996, 37, 6811.
16. (h) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J.Org.Chem. 1996, 61 , 9280.
17. For representative examples of N-alkyl- and aryl-4-alkylideneoxazolidin-2-ones syntheses see : (a) Shacht, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991. (b) Cameron, M.D. US Patent 2844590, 1958; Chem Abstr. 1959, 53, 2254g. (c) Stoffel, P.J.; Speziale, A.J. J.Org. Chem. 1963, 28, 2814. (d) Dimroth, P.; Pasedach, H.; Schefczik, E. German Patent 11515507, 1963; Chem Abstr. 1964, 60 , 2934f. (e) Fournier, J.; Bruneau, C.; Dixneuf, P.M. Tetrahedron Lett. 1990, 31, 1721.
18. For representative examples of N-alkyl- and aryl-4-alkylideneoxazolidin-2-ones syntheses see : (a) Shacht, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991. (b) Cameron, M.D. US Patent 2844590, 1958; Chem Abstr. 1959, 53, 2254g. (c) Stoffel, P.J.; Speziale, A.J. J.Org. Chem. 1963, 28, 2814. (d) Dimroth, P.; Pasedach, H.; Schefczik, E. German Patent 11515507, 1963; Chem Abstr. 1964, 60 , 2934f. (e) Fournier, J.; Bruneau, C.; Dixneuf, P.M. Tetrahedron Lett. 1990, 31, 1721.
19. For representative examples of N-alkyl- and aryl-4-alkylideneoxazolidin-2-ones syntheses see : (a) Shacht, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991. (b) Cameron, M.D. US Patent 2844590, 1958; Chem Abstr. 1959, 53, 2254g. (c) Stoffel, P.J.; Speziale, A.J. J.Org. Chem. 1963, 28, 2814. (d) Dimroth, P.; Pasedach, H.; Schefczik, E. German Patent 11515507, 1963; Chem Abstr. 1964, 60 , 2934f. (e) Fournier, J.; Bruneau, C.; Dixneuf, P.M. Tetrahedron Lett. 1990, 31, 1721.
20. For representative examples of N-alkyl- and aryl-4-alkylideneoxazolidin-2-ones syntheses see : (a) Shacht, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991. (b) Cameron, M.D. US Patent 2844590, 1958; Chem Abstr. 1959, 53, 2254g. (c) Stoffel, P.J.; Speziale, A.J. J.Org. Chem. 1963, 28, 2814. (d) Dimroth, P.; Pasedach, H.; Schefczik, E. German Patent 11515507, 1963; Chem Abstr. 1964, 60 , 2934f. (e) Fournier, J.; Bruneau, C.; Dixneuf, P.M. Tetrahedron Lett. 1990, 31, 1721.
21. For representative examples of N-alkyl- and aryl-4-alkylideneoxazolidin-2-ones syntheses see : (a) Shacht, N.; Bagnell, J.J., Jr. J. Org. Chem. 1963, 28, 991. (b) Cameron, M.D. US Patent 2844590, 1958; Chem Abstr. 1959, 53, 2254g. (c) Stoffel, P.J.; Speziale, A.J. J.Org. Chem. 1963, 28, 2814. (d) Dimroth, P.; Pasedach, H.; Schefczik, E. German Patent 11515507, 1963; Chem Abstr. 1964, 60 , 2934f. (e) Fournier, J.; Bruneau, C.; Dixneuf, P.M. Tetrahedron Lett. 1990, 31, 1721.
22. For examples of 4-alkylidene-3-tosyloxazolidin-2-ones syntheses see : (a) Kimura, M.; Kure, S.; Yoshida, Z.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1990, 31, 4887. (b) Ohe, K.; Ishihara, T.; Chatani, N.; Kawasaki, Y.; Murai, S. J. Org. Chem. 1991, 56, 2267.
23. For examples of 4-alkylidene-3-tosyloxazolidin-2-ones syntheses see : (a) Kimura, M.; Kure, S.; Yoshida, Z.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1990, 31, 4887. (b) Ohe, K.; Ishihara, T.; Chatani, N.; Kawasaki, Y.; Murai, S. J. Org. Chem. 1991, 56, 2267.
24. 2-Propynyl tosylcarbamates 1a-d were easily prepared from propargyl alcohols, p-toluenesulfonylisocyanate in the presence of catalytic amounts of triethylamine, see : ref 5b.
25. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
26. Similar results could be obtained using tetrabutylammonium chloride. We preferred to choose the less expensive TEBA (benzyltriethylammonium chloride). The beneficial effect of the use of quaternary ammonium chlorides salts in our palladium-catalyzed cyclisation was already observed see ref 2a.
27. 4 condensed in vacuo and the residue was chromatographed on silica gel to give the pure (E)-4-arylidene-3-tosyloxazolidin-2-one 3a (250 mg , 76%).
28. 1H NMR data with those given in the litterature for the same compounds : cf ref 5b
29. Monteiro, N. ; Goré, J. ; Balme, G. Tetrahedron 1992, 48, 10103.
30. Scott, W.J.; Stille, J.K. J.Am.Chem.Soc. 1986, 108, 3033. Echavarren, A.M.; Stille, J.K. J.Am.Chem.Soc. 1987, 109, 5478. Anerson, C.M.; Hallberg, A. J. Org. Chem. 1988, 53, 2122. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525.
31. Scott, W.J.; Stille, J.K. J.Am.Chem.Soc. 1986, 108, 3033. Echavarren, A.M.; Stille, J.K. J.Am.Chem.Soc. 1987, 109, 5478. Anerson, C.M.; Hallberg, A. J. Org. Chem. 1988, 53, 2122. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525.
32. Scott, W.J.; Stille, J.K. J.Am.Chem.Soc. 1986, 108, 3033. Echavarren, A.M.; Stille, J.K. J.Am.Chem.Soc. 1987, 109, 5478. Anerson, C.M.; Hallberg, A. J. Org. Chem. 1988, 53, 2122. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525.
33. Scott, W.J.; Stille, J.K. J.Am.Chem.Soc. 1986, 108, 3033. Echavarren, A.M.; Stille, J.K. J.Am.Chem.Soc. 1987, 109, 5478. Anerson, C.M.; Hallberg, A. J. Org. Chem. 1988, 53, 2122. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525.
34. Scott, W.J.; Stille, J.K. J.Am.Chem.Soc. 1986, 108, 3033. Echavarren, A.M.; Stille, J.K. J.Am.Chem.Soc. 1987, 109, 5478. Anerson, C.M.; Hallberg, A. J. Org. Chem. 1988, 53, 2122. Friess, B.; Cazes, B.; Goré, J. Tetrahedron Lett. 1988, 29, 4089. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F. Tetrahedron 1991, 47, 1525.
35. A similar and complementary work has been developed independently and simultaneously by A. Arcadi, see preceding paper. Arcadi, A. Synlett 1997, 941.