Palladium(0)-catalyzed coupling reactions of an N-tosylpyrrolidinone-derived enamine triflate

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3561-3564

  Bernabé, Pablo ^a   Rutjes, Floris P J T ^a   Hiemstra, Henk ^a   Speckamp, W Nico ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029897096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00612-0     Document Type: Article

References (30)

1. For a review on vinyl triflate chemistry, see: Ritter, K. Synthesis 1993, 735.
2. (a) Stille, J.K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508;
3. (b) Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033.
4. De Meijere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
5. See e.g.: Lipshutz, B.H.; Elworthy, T.R. J. Org. Chem. 1990, 55, 1695.
6. Cintas, P. Synthesis 1992, 248.
7. For cuprate additions, see e.g. (a) Tsushima, K.; Murai, A. Chem. Lett. 1990, 761.
8. (b) Nicolaou, K.C.; Reddy, K.R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558. For cuprate additions to thiolactone-derived vinyl triflates, see:
9. (c) O'Neil, I.A.; Hamilton, K.M.; Miller, J.A.; Youmg, R.J. Synlett 1995, 151; For Nozaki-Hiyama couplings, see:
10. (d) Nicolaou, K.C.; Theodorakis, E.A.; Rutjes, F.P.J.T.; Sato, M.; Tiebes, J.; Xiao, X.-Y.; Hwang, C.-K.; Duggan, M.E.; Yang, Z.; Couladouros, E.A.; Sato, F.; Shin, J.; He, H.-M.; Bleckman, T. J. Am. Chem. Soc. 1995, 117, 10239.
11. (a) Okita, T.; Isobe, M. Tetrahedron 1995, 3737;
12. (b) Foti, C.J.; Comins, D.L. J. Org. Chem. 1995, 60, 2656.
13. See e.g.: (a) Romagnoli, R.; Roos, E.C.; Hiemstra, H.; Moolenaar, M.J.; Speckamp, W.N.; Kaptein, B.; Schoemaker, H.E. Tetrahedron Lett. 1994, 35, 1087;
14. (b) Hopman, J.C.P.; Hiemstra, H.; Speckamp, W.N. J. Chem. Soc. Chem. Commun. 1995, 617;
15. (c) Moolenaar, M.J.; Speckamp, W.N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem. Int. Ed. Engl. 1995, 34, 2391.
16. This is complementary with observations of Isobe 7a and Comins, 7b who state that the unsubstituted N-benzoyl-2-pyrrolidinone-derived vinyl triflate is highly unstable.
17. 2: 368.9953.
18. McMurry, J.E.; Scott, W.J. Tetrahedron Lett. 1983, 24, 919.
19. Comins, D.L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
20. Scott, W.J.; Crisp, G.P.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630.
21. 13C NMR, high resolution mass spectral data).
22. 2S: 255.0097.
23. A similar example in which a triflate is replaced by a cyanide has been reported: Sisti, N.J.; Fowler, F.W.; Grierson, D.S. Synlett 1991, 816.
24. Farina, V.; Kapodia, S.; Krishnan, B.; Wang, C.; Liebeskind, L.S. J. Org. Chem. 1994, 59, 5905.
25. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
26. 2S: 247.0667.
27. Solberg, J.; Undheim, K. Acta Chem, Scand. Ser. B. 1989, 43, 62.
28. Farina, V.; Krishnan, B.; Marshall, D.R.; Roth, G.P. J. Org. Chem. 1993, 58, 5434.
29. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109.
30. Scott, W.J.; McMurray, J.E. Acc. Chem. Res. 1988, 21, 47.