A dramatic effect of the reaction conditions on the course of a palladium-catalyzed cyclization of an alkene bearing a vinyl bromide and a nucleophile: A new route to the trans-hydrindane system

Synlett

Volumn , Issue 9, 1998, Pages 995-997

  Coudanne, Isabelle ^a   Castro, Jaume ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003131844     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1829     Document Type: Article

References (29)

1. (a) Nara, S.; Toshima, H.; Ichihara, A. Tetrahedron Lett. 1996, 37, 6745.
2. (b) Tamao, K.; Nagata, Y. Ito; Maeda, K.; Shiro, M. Synlett 1994, 257.
3. (c) Satoh, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1991, 56, 2278 and references cited therein.
4. (d) Shibasaki, M.; Boden, J.D.; Kojima, A. Tetrahedron 1997, 53, 7371.
5. Coudame, I.; Balme, G. Synlett 1998, 998.
6. (a) Vittoz, P.; Bouyssi, D.; Traversa, C.; Goré, J.; Balme, G. Tetrahedron Lett. 1994, 35, 1871.
7. (b) Bouyssi, D.; Coudanne, I.; Uriot, H.; Goré, J.; Balme, G. Tetrahedron Lett. 1994, 35, 1871.
8. Interestingly, recent studies by Weinreb's group have shown that a novel variation of the Heck reaction can be applied on substrates which contain a vinyl halide, an olefin and a nucleophile leading to various carbo- and heterobicyclic compounds. Nevertheless, it is important to note that the Weinreb's three component reactions were never applied to substrates which could be involved in the Wacker-type reaction: (a) Nylund, C.S.; Klopp, J.M.; Weinreb, S.M. Tetrahedron Lett. 1994, 35, 4287.
9. (b) Nylund, C.S.; Smith, D.T.; Klopp, J.M.; Weinreb, S.M. Tetrahedron 1995, 51, 9301.
10. (a) Shi, L.; Namla, C.K.; Mak, K.T.; Kao, L.; Xu, Y.; Heck, R.F. J. Org. Chem. 1983, 48, 3894.
11. (b) Grigg, R.; Stevenson, P.; Worakun, T.J. Tetrahedron 1988, 44, 2033.
12. (c) Meyer, F. E.; Ang, K.H.; Steinig, A.C.; de Meijere, A. Synlett 1994, 191.
13. (d) Henniges, H.; Meyer, F.E.; Schick, U.; Funke, F.; Parsons, P.J.; de Meijere, A. Tetrahedron 1996, 52, 11503.
14. Ireland, R.E.; Norbeck, D.W. J. Org. Chem. 1985, 50, 2198.
15. Ziegler, F.E. Chem. Rev. 1988, 88, 1423.
16. Kara, S.; Dojo, H.; Takinani, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
17. The product ratio was determined by integration of the vinyl proton peaks in the H NMR spectrum.
18. 3) 173, 172.2, 147.8, 109.4, 61.7, 52.8, 52.4, 52.1. 42.7, 37.2, 34.2, 33.1, 32.3, 30.9. MS, m/z (relative intensity): 220 (23), 192 (43), 160 (31), 145 (27), 133 (46), 120 (100), 106 (96), 91 (49), 77 (27), 59 (36), 41 (29), 39 (20).
19. Bond distances (Å) and bond angles (°) of compound 4: O1-C11 1.201(3), C1-C10 1.573(4), C4-C6 1.510(5), O2-C11 1.319(4), C1-C11 1.519(4), C6-C7 1.540(4), O2-C12 1.454(4), C1-C13 1.507(4), C7-C8 1.517(4), O3-C13 1.197(3), C2-C3 1.518(3), C8-C9 1.550(4), O4-C13 1.316(3), C2-C8 1.530(4), C9-C10 1.535(5), O4-C14 1.456(4), C3-C4 1.514(4), C1-C2 1.563(4), C4-C5 1.314(4), C11-O2-C12 115.7(3), C3-C2-C8 111.4(2), C8-C9-C10 103.0(3), C13-O4-C14 116.4(2), C2-C3-C4 108.3(2), C1-C10-C9 107.0(2), C2-C1-C10 103.1(2), C3-C4-C5 122.9(3), O1-C11-O2. 124.0(3), C2-C1-C11 109.6(2), C3-C4-C6 115.2(2), O1-C11-C1 124.6(3), C2-C1-C13 112.1(2), C5-C4-C6 121.9(3), O2-C11-C1 111.3(2), C10-C1-C11 111.0(2), C4-C6-C7 111.2(3), O3-C13-O4 123.0(3), C10-C1-C13 110.3(2), C6-C7-C8 109.0(3), O3-C 13-C1 125.4(3), C11-C1-C13 110.5(2), C2-C8-C7 110.6(2), O4-C13-C1 111.5(2), C1-C2-C3 119.4(2), C2-C8-C9 101.1(2), C1-C2-C8 104.1(2), C7-C8-C9 116.1(3).
20. (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
21. (b) Jeffery, T. Synthesis 1987, 70.
22. Larock, R.C.; Baker, B.E. Tetrahedron Lett. 1988, 29, 905.
23. 1H NMR spectroscopy.
24. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
25. + 252 (7), 220 (7), 192 (53), 160 (16), 145 (16), 132 (36), 120 (100), 106 (36), 91 (41), 77 (30), 59 (31), 41 (23).
26. See for example: Boden C.; Pattenden, G. Contemporary Organic Synthesis 1996, 3, 19.
27. Balme, G.; Bouyssi, D.; Goré, J.; Faure, R.; Van Hemelryck, B. Tetrahedron 1992, 48, 3891.
28. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis, John Wiley & Sons, Chichester: 1995; p. 156;
29. (b) Negishi, E.I.; Copéret, C.; Ma, S.; Liou, S.Y.; Liu, F. Chem. Rev. 1996, 96, 365.