Directed palladium-catalyzed cascade cyclization as an approach to trans- and cis-hexahydro-1H-benz[f]indenes

Synlett

Volumn , Issue 9, 1998, Pages 998-1000

  Coudanne, Isabelle ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003113486     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1828     Document Type: Article

References (24)

1. For leading references see : a) Cascade reactions, Tetrahedron Symposia-in-print 1996, 52.
2. b) Negishi, E.I. Pure Appl. Chem. 1992, 64, 323.
3. c) Overman, L.E.; Abelman, M.M.; Kucera, D.J.; Tran, V.D.; Ricca, D.J. Pure Appl. Chem. 1992, 64, 1813.
4. d) Hok, T.L. Tandem Organic Reactions, Wiley Interscience, New York: 1992.
5. e) Tietze, L.F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
6. f) de Meijere, A.; Meyer, F.E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
7. a) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1991, 47, 6293.
8. b) Balme, G.; Bouyssi, D.; Faure, R.; Goré, J.; Van Hemelryck, B. Tetrahedron 1992, 48, 3881.
9. c) Bouyssi, D.; Balme, G.; Fournet, G.; Monteiro, N.; Goré, J. Tetrahedron Lett. 1991, 32, 1641.
10. a) Vittoz, P.; Bouyssi, D.; Traversa, C.; Goré, J.; Balme, G. Tetrahedron Lett. 1994, 55, 1871.
11. b) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
12. c) Cavicchioli, M.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429.
13. d) Cavicchioli, M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron 1996, 52, 11463.
14. e) Bruyère, D.; Gaignard, G.; Bouyssi, D.; Balme, G.; Lancelin, J.M. Tetrahedron Lett. 1997, 38, 827.
15. For a recent synthesis of trans-hexahydro-1H-benz[f]indene via a radical cyclization see: (a) Pal, S.; Mukherjee, M.; Podder, D.; Mukherjee, A.K.; Ghatak, U.R. J. Chem. Soc., Chem. Commun. 1991, 1591.
16. (b) Pal, S.; Mukhopadhyaya, K.; Ghatak, U.R. J. Org. Chem. 1994, 59, 2687.
17. The acetylenic alcohol 5 was previously prepared by our group, see ref. 3d.
18. 2 (5 mol%) and dppe (5 mol %) in the presence of 1-heptene (10 mol%, NMP, 50°C) until a homogeneous dark red solution was obtained.
19. 3); 3.40-3.27 (1H, m, C(9eq)-H); 2.8-2.6 (2H, m, C(4eq)-H, C(2eq)-H), 2.43 (1H, ddd, J =11.8, 12.4. 4.7 Hz, C(9a)-H); 2.27 (1H, dd, J =15.8, 11.2 Hz, C(4ax)-H); 2.11 (1H, ddd, J =14, 10.8, 3 Hz, C(2ax)-H); 2.1-1.85 (2H, m, C(3a), (3eq)-H); 1.1-1.0 (1H, m, C-3ax-H).
20. Hoffmann, R.W. Chem. Rev. 1989, 89, 875.
21. The beneficial effect in the use of 1-methyl-2-pyrrolidinone in our palladium-catalyzed cyclization has already been observed: Bouyssi, D.; Coudanne, I.; Uriot, H.; Goré, J.; Balme, G. Tetrahedron Lett. 1995, 36, 8019 and ref. 2b and 3e.
22. 2).
23. Cis-4 is homogeneous by GC while a coinjection of trans-4 with a sample of cis-4 shows two distinct peaks.
24. Metzger, P.; Casadevall, E.; Pouet, M. J. Org. Magn. Reson. 1982, 91, 229.