New method for the synthesis of functionalized 1,3-bis-exocyclic dienes via a palladium-catalyzed reaction. Scope and synthetic applications

Synthesis

Volumn , Issue 2, 2005, Pages 311-329

  Lomberget, Thierry ^a   Bouyssi, Didier ^a,b   Balme, Geneviève ^a,b,c  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ DE LYON   (France)

^c UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Cyclization; Electrocyclization; Enynes; Exocyclic dienes; Palladium

Indexed keywords

ARYL IODIDES; CARBON NUCLEOPHILE; CONJUGATED ENYNES; VINYL HALIDES;

CARBON; CATALYSIS; IODINE COMPOUNDS; OLEFINS; PALLADIUM; STEREOCHEMISTRY;

REACTION KINETICS;

ALKADIENE; CARBON; CYCLOHEXYLAMINE DERIVATIVE; CYCLOPENTANE DERIVATIVE; HALIDE; IODIDE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13844289246     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834879     Document Type: Review

References (67)

1. (a) Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1 and 2; Negishi, E.-I., Ed.; John Wiley and Sons: New York, 2002.
2. (b) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
3. (c) de Meijere, A.; Bräse, S. J. Organomet. Chem. 1999, 576, 88.
4. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 99.
5. (e) Tetrahedron Symposium-in-Print 1996, 52, Vol. 35.
6. (f) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: Chichester, 1995.
7. (g) Bunce, R. A. Tetrahedron 1995, 51, 13103.
8. (h) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
9. (i) Ho, T. L. Tandem Organic Reactions; Wiley Interscience: New York, 1992.
10. (j) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
11. (k) Negishi, E.-I. Pure Appl. Chem. 1992, 64, 323.
12. (a) Balme, G.; Bouyssi, D.; Lomberget, T.; Monteiro, N. Synthesis 2003, 2115.
13. (b) For reactions involving carbonucleophiles, see: Balme, G.; Bouyssi, D.; Monteiro, N. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley Interscience: New York, 2002, 2245.
14. (c) For oxygen nucleophile, see: Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley Interscience: New York, 2002, 2193-2210.
15. (d) For nitrogen nucleophiles, see: Cacchi, S.; Marinelli, F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley Interscience: New York, 2002, 2227-2244.
16. (a) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
17. (b) Coudanne, I.; Balme, G. Synlett 1998, 998.
18. (c) Bruyère, D.; Gaignard, G.; Bouyssi, D.; Balme, G.; Lancelin, J. M. Tetrahedron Lett. 1997, 38, 827.
19. (d) Garçon, S.; Vassiliou, S.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 4069, and references cited therein.
20. For some examples using organometallic compounds, see: (a) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788.
21. (b) Bailey, W. F.; Wachter-Jurcsak, N. M.; Pineau, M. R.; Ovaska, T. V.; Warren, R. R.; Lewis, C. E. J. Org. Chem. 1996, 61, 8216.
22. (c) Urabe, H.; Nakajima, R.; Sato, F. Org. Lett. 2000, 2, 3481.
23. (d) Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1502.
24. (e) Meyer, F. E.; Ang, K. H.; Steinig, A. G.; de Meijere, A. Synlett 1994, 191.
25. (f) Wang, X.; Chakrapani, H.; Madine, J. W.; Keyerleber, M. A.; Widenhoefer, R. A. J. Org. Chem. 2002, 67, 2778.
26. (g) Mori, M.; Kozawa, Y.; Nishida, M.; Kanamaru, M.; Onozuka, K.; Takimoto, M. Org. Lett. 2000, 2, 3245.
27. (h) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923.
28. (i) Grigg, R.; Savic, V. Tetrahedron Lett. 1996, 37, 6565.
29. (j) Meyer, F. E.; Henniges, H.; de Meijere, A. Tetrahedron Lett. 1992, 33, 8039.
30. (k) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491.
31. For the preliminary communication concerning this work, see: Lomberget, T.; Bouyssi, D.; Balme, G. Synlett 2002, 1439.
32. (a) Cousseau, J. Synthesis 1980, 805.
33. (b) Barton, T. J.; Lin, J.; Ijadi-Maghsoodi, S.; Power, M. D.; Zhang, X.; Ma, Z.; Shimizu, H.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 11695.
34. 2 (5 mol%) and dppe (5 mol%) in the presence of 1-heptene (10 mol%, THF 50 °C) until a homogeneous dark red solution was obtained.
35. 2 with n-BuLi has been found particularly effective in related carbopalladation reactions: (a) See ref. 3d.
36. (b) Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 175.
37. 2 with n-BuLi, see: Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 1670.
38. The demethoxycarbonylation of malonate ester using Krapcho's conditions generally needs prolonged heating in polar solvent: (a) Krapcho, A. P. Synthesis 1982, 805.
39. (b) Krapcho, A. P. Synthesis 1982, 893, the strain generated by the two contiguous exocyclic double bonds and the malonate could explain these rather mild conditions.
40. The difference in the rate of cyclization between a malononitrile and dimethylmalonate or methylcyanoacetate derivative was already observed. See: Bouyssi, D.; Coudanne, I.; Uriot, H.; Gore, J.; Balme, G. Tetrahedron Lett. 1995, 36, 8019.
41. Bouyssi, D.; Balme, G.; Fournet, G.; Monteiro, N.; Goré, J. Tetrahedron Lett. 1991, 32, 1641.
42. (a) Fournet, G.; Balme, G.; van Hemelryck, B.; Goré, J. Tetrahedron Lett. 1990, 31, 5147.
43. (b) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1991, 47, 6293.
44. (c) Coudanne, I. PhD Thesis; Université Claude Bernard: Lyon, 1997.
45. Klusener, P. A. A.; Kulik, W.; Brandsma, L. J. Org. Chem. 1987, 52, 5261.
46. 1H NMR.
47. Gregory, K.; Bremer, M.; vonRagué Schleyer, P.; Klusener, P. A. A.; Brandsma, L. Angew. Chem., Int. Ed. Engl. 1989, 28, 1224.
48. Koradin, C.; Rodriguez, A.; Knochel, P. Synlett 2000, 1452.
49. For an other example of a copper-free Sonogashira coupling see: Böhm, V. P. W.; Hermann, W. A. Eur. J. Org. Chem. 2000, 3679.
50. The synthetic utility of these dienic substrates 7e and 7f having an allylic sulfone would be of prime interest since they may allow further functionalization by allylic substitution. See: (a) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993.
51. (b) Trost, B. Bull. Chem. Soc. Jpn. 1988, 61, 107.
52. (c) Woods, M.; Monteiro, N.; Balme, G. Eur. J. Org. Chem. 2000, 1711.
53. (d) Clique, B.; Vassiliou, S.; Monteiro, N.; Balme, G. Eur. J. Org. Chem. 2002, 1493.
54. For related examples of palladium-catalyzed reaction combined with 6-π electrocyclization processes, see: (a) See ref. 4h-k.
55. (b) Gilchrist, T. L.; Summersell, R. J. Tetrahedron Lett. 1987, 28, 1469.
56. (c) Gilchrist, T. L.; Healy, M. A. M. J. Chem. Soc., Perkin Trans. 1 1992, 749.
57. (d) von Zezschwitz, P.; Petty, F.; de Meijere, A. Chem.-Eur. J. 2001, 7, 4035.
58. Similar results were recently reported for palladium catalyzed tandem cyclization/coupling reactions involving commercial β-bromostyrene: (a) See ref. 8b.
59. (b) Arcadi, A.; Cacchi, S.; Cassetta, A.; Fabrizi, G.; Parisi, L. M. Synlett 2001, 1605.
60. Lomberget, T.; Chataigner, I.; Bouyssi, D.; Maddaluno, J.; Balme, G. Tetrahedron Lett. 2004, 45, 3437.
61. Lomberget, T.; Bentz, E.; Bouyssi, D.; Balme, G. Org. Lett. 2003, 5, 2055.
62. (a) Lin, W.-H.; Fang, J.-M.; Cheng, Y.-S. Phytochemistry 1995, 40, 871.
63. (b) Ohtsu, H.; Iwamoto, M.; Ohishi, H.; Matsunaga, S.; Tanaka, R. Tetrahedron Lett. 1999, 40, 6419.
64. (c) Kawazoe, K.; Yamamoto, M.; Takaishi, Y.; Honda, G.; Fujita, T.; Sezik, E.; Yesilada, E. Phytochemistry 1999, 50, 493.
65. Marvell, E. N. Thermal Electrocyclic Reactions; Academic Press: New York, 1980.
66. Burchat, A. F.; Chong, J. M.; Nielsen, N. J. Organomet. Chem. 1997, 542, 281.
67. Coulson, D. R. Inorg. Synth. 1974, 13, 121.