Heck reaction versus free radical reaction for the synthesis of spiro[indoline-2,4′-piperidines]

Synlett

Volumn , Issue 3, 1998, Pages 251-252

  Cossy, Janine ^a   Poitevin, Christophe ^a,b   Pardo, Domingo Gomez ^a   Peglion, Jean Louis ^b   Dessinges, Aimée ^b  

^a CNRS   (France)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005253608     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1622     Document Type: Article

References (35)

1. Chambers, M. S.; Baker, R.; Billigton, D. C.; Knight, A. K.; Middlemiss, D. N.; Wong, E. H. F. J. Med. Chem. 1992, 35, 2033.
2. Evans, B. E.; Leighton, J. L.; Ritle, K. E.; Gilbert, K. F.; Lundell, G. F.; Gould, N. P.; Hobbs, D. W.; DiPardo, R. M.; Veber, D. F.; Pettibone, D. J.; Clineschmidt, B. V.; Anderson, P. S.; Freidinger, R. M. J. Med. Chem. 1992, 35, 3919.
3. Palmisano, G.; Annunziata, R.; Papeo, G.; Sisti, M. Tetrahedron: Asymmetry 1996, 7, 1.
4. Clark, A. J.; Davies, D. I.; Jones, K.; Millbanks, C. J. Chem. Soc., Chem. Commun. 1994, 41.
5. Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakum, T. Tetrahedron 1996, 52, 11479.
6. Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 7471.
7. Grigg, R.; Rasui, R.; Redpath, J.; Wilson, D. Tetrahedron Lett. 1996, 37, 4609.
8. Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. J. Chem. Soc., Chem. Commun. 1995, 1135.
9. Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: London, 1985.
10. Tsuji, J. Synthesis with Palladium Compounds; Springer-Verlag: Berlin, 1980.
11. Harrington P. J. Transition Metals in Total Synthesis; Wiley-Interscience: New York, 1990.
12. Heck, R. F. Org. React. 1982, 27, 345.
13. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
14. Negishi, E.; Copéret, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
15. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
16. Abelman, M. M.; Overman, L. E.; Tran, V. D. J. Am. Chem. Soc. 1990, 112, 6959.
17. Negishi, E. I.; Zhnag, Y.; O'Connor, B. Tetrahedron Lett. 1988, 29, 2915.
18. Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919.
19. Neghishi, E. I.; N'Guyen, T.; O'Connor, B. Heterocycles 1989, 28, 55.
20. Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakum, T. Tetrahedron 1991, 47, 9703.
21. Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Petit, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177.
22. Grigg, R.; Stevenson, P.; Worakum, T. J. Chem. Soc., Chem. Commun. 1984, 1073.
23. Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramassubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. I 1984, 1745.
24. Grigg, R.; Stevenson, P.; Worakum, T. Tetrahedron 1988, 44, 2033.
25. Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakum, T. Tetrahedron 1990, 46, 4003.
26. +., 57); 244 (31); 157 (61); 156 (85); 144 (100); 143 (80); 57 (92).
27. HPLC: Lichroprep Si 60 (C); toluent/TEA: 100/0.25; 5.0 mL/ min; λ= 350 nm
28. Beckwith, A. L. J.; Gara, W. B. J. Chem. Soc., Perkin Trans. II 1975, 593.
29. Beckwith, A. L. J.; Gara, W. B. J. Chem. Soc., Perkin Trans. II 1975, 795.
30. Beckwith, A. L. J.; Meijs, G. F. J. Chem. Soc., Chem. Commun. 1981, 136.
31. Wolff, S.; Hoffman, H. M. R. Synthesis 1988, 760.
32. Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796.
33. Chen, H. S.; Abraham, J. A. Tetrahedron Lett. 1996, 37, 5233.
34. For spiroheterocycles formation see: Jones, K.; Thompson, M.; Wright, C. J. Chem. Soc., Chem. Commun. 1986, 115.
35. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.