Regiochemical control and suppression of double bond isomerization in the heck arylation of 1-(methoxycarbonyl)-2,5-dihydropyrrole

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4756-4763

  Sonesson, Clas ^a   Larhed, Mats ^b   Nyqvist, Camilla ^a   Hallberg, Anders ^b  

^a Medicinal Chemistry Unit   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001113064     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952112s     Document Type: Article

References (116)

1. (a) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21.
2. (b) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529.
3. (a) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417.
4. (b) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188.
5. (c) Killers, S.; Reiser, O. Tetrahedron Lett. 1993, 33, 5265.
6. (d) Hillers, S.; Reiser, O. Synlett 1995, 153.
7. (a) Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464.
8. (b) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267.
9. (c) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087.
10. Harrington, P. J.; DiFiore, K. A. Tetrahedron Lett. 1987, 28, 495.
11. Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.
12. Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015.
13. (a) Hacksell, U.; Arvidsson, L.-E.; Svensson, U.; Nilsson, L. G.; Sanchez, D.; Wikström, H.; Lindberg, P.; Hjorth, S.; Carlsson, A. J. Med. Chem. 1981, 24, 1475.
14. (b) Hjorth, S.; Carlsson, A.; Clark, D.; Svensson, K.; Wikström, H.; Sanchez, D.; Lindberg, P.; Hacksell, U.; Arvidsson, L.-E.; Johansson, A.; Nilsson, J. L. G. Psychopharmacology 1983, 81, 89.
15. (c) Tamminga, C. A.; Cascella, N. G.; Lahti, R. A.; Lindberg, M.; Carlsson, A. J. Neural Transm. [GenSect] 1992, 88, 165.
16. Sonesson, C.; Lin, C.-H.; Hansson, L.; Waters, N.; Svensson, K.; Carlsson, A.; Smith, M. W.; Wikström, H. J. Med. Chem. 1994, 37, 2735.
17. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
18. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
19. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
20. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
21. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
22. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
23. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
24. For reviews on the Heck reaction see; (a) Heck, R. F. Org React. 1982, 27, 345. (b) Trost, B. M.; Verhoeven, T. R. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 854. (c) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press; London, 1985; pp 276. (d) Heck, R. F. Comprehensive Organic Synthesis; Trost, B. M., Flemmmg, I., Eds.; Pergamon Press: Oxford 1991; Vol. 4, pp 833. (e) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (f) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2. (g) For Heck arylation of heteroatom-substituted double bonds see Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Chemistry; John Wiley & Sons: Chichester, 1995; pp 125-163. (h) Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
25. We recently reported that 8 was conveniently prepared from 4a under Heck reaction conditions omitting aryl halide. Sonesson, C.; Hallberg, A. Tetrahedron Lett. 1995, 36, 4505.
26. (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
27. (b) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. For recent applications of silver additives in intramolecular Heck reactions see:
28. (c) Ahimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571.
29. (d) Larock, R. C. Pure Appl. Chem. 1990, 62, 653.
30. (e) Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2589.
31. (f) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593.
32. (g) Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4965.
33. (h) Sakamoto, T.; Kondo, Y.; Uchiyama, M.; Yamanaka. H. J. Chem. Soc., Perkin Trans. 1 1993, 1941.
34. (i) Jin, Z.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5205.
35. (j) Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089.
36. (k) Steinig, A. G.; Bräse, S.; de Meijere, A. 8th IUPAC Symposium on Organo-Metallic Chemistry directed towards Organic Synthesis, Santa Barbara, 1995, Abstr. No. 241.
37. A 0.7 equiv amount of silver carbonate was the minimum amount needed to fully suppress the formation of 6a.
38. 3, were superior to the bidentate ligands with regard to regioselectivity and yield.
39. (a) Echavarren, A. M. and Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
40. (b) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
41. (c) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
42. (d) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
43. (e) Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285.
44. (f) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
45. No conversion of the aryl triflate occurred with dppp in presence of chloride, as expected from recent findings. See refs 16 and 35d.
46. Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796.
47. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
48. (a) Dukat, N.; Damaj, M. I.; Glassco, W.; Dumas, D.; May, E. L.; Martin, B. R. Med. Chem. Res. 1994, 4, 131.
49. (b) Ber. Dtsch. Chem. Ges. B 1938, 71, 1276.
50. (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54,4738.
51. (b) Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
52. (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322.
53. (a) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846.
54. (b) Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6949.
55. Ozawa, F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2505.
56. Asymmetric arylation of the cyclic vinyl ether 4H-1,3-dioxin with (R)-BINAP as ligand has been achieved in 43% ee utilizing iodobenzene/silver carbonate. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845.
57. Koga, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1994, 35, 1227.
58. Sonesson, C.; Wikström, H.; Smith, M. W.; Svensson, K.; Carlsson, A.; Waters, N. Bioorg. Med. Chem. Lett., to be submitted.
59. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl. See. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
60. Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
61. DMF was also found to be superior to benzene in the asymmetric arylation of 4H-1,3-dioxin. See ref 22.
62. The acetate ion is considered to possess an intermediately strong dissociating ability to Pd(II), with respect to the easily dissociated triflate ion and the more strongly complexed halide ions. See refs 16 and 35d.
63. (a) Suppression of double bond migration by acetate addition in Heck reactions has been reported. See, Laschat, S.; Narjes, F.; Overman, L. E. Tetrahedron 1994, 50, 347. See also ref 2b and 5.
64. 2/DPPP/ KOAc (2.0 equiv).
65. 1 coordination mode and in the chelating mode. Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465.
66. (a) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371.
67. (b) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 3388.
68. 2/(R)-BINAP/HOAc (1.0 equiv) were employed. All three reactions at 80°C afforded after 18 h an almost identical 11/89 mixture of 5b and 6b, demonstrating the higher reactivity of 8 irrespective of the acetate concentration. This result corroborate the proposal that the increased 5b/6b ratio in the asymmetric arylation is due to acetate-mediated suppression of isomerization.
69. 3 in controlling the regioselectivity with aryl halides.
70. 2 with cyclohexene in the presence of base and BINAP did not improve the ee. See ref 31a.
71. Thallium(I) salts have been introduced and proved to be very useful in Pd-catalyzed reactions. (a) Grigg, R.; Loganathan, V.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1890, 31, 6573. (b) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687. (c) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R. and Fiorani, T. J. Org. Chem. 1991, 56, 261. (d) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
72. Thallium(I) salts have been introduced and proved to be very useful in Pd-catalyzed reactions. (a) Grigg, R.; Loganathan, V.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1890, 31, 6573. (b) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687. (c) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R. and Fiorani, T. J. Org. Chem. 1991, 56, 261. (d) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
73. Thallium(I) salts have been introduced and proved to be very useful in Pd-catalyzed reactions. (a) Grigg, R.; Loganathan, V.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1890, 31, 6573. (b) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687. (c) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R. and Fiorani, T. J. Org. Chem. 1991, 56, 261. (d) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
74. Thallium(I) salts have been introduced and proved to be very useful in Pd-catalyzed reactions. (a) Grigg, R.; Loganathan, V.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1890, 31, 6573. (b) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687. (c) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R. and Fiorani, T. J. Org. Chem. 1991, 56, 261. (d) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481.
75. In solution the triflate anion is not coordinated to palladium(II). See ref 14d and Decker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics 1992, 11, 1598.
76. Saá, J. M.; Dopico, M.; Martorell, G.; García-Raso, A. J. Org. Chem. 1990, 55, 991.
77. For olefin as reducing agent see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571. For phosphine as reducing agent see; (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
78. For olefin as reducing agent see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571. For phosphine as reducing agent see; (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
79. For olefin as reducing agent see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571. For phosphine as reducing agent see; (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
80. For olefin as reducing agent see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571. For phosphine as reducing agent see; (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818.
81. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513. See also ref 26.
82. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; John Wiley & Sons Inc: New York, 1992; p 8.
83. (b) For Pd(II)-catalyzed olefin isomerization see: Sen, A.; Lai, T.-W. Inorg. Chem. 1984, 23, 3257.
84. (c) For isomerization of N-allylamides catalyzed by other transition metal complexes see: Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139.
85. (a) Wanner, K. Th.; Kartner, A. Heterocycles 1987, 26, 917.
86. (b) Wanner, K. Th.; Kartner, A. Arch. Pharm. (Weinheim) 1987, 320, 1050.
87. Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Chem. Soc., Chem. Commun. 1986, 1338.
88. 2. See: (a) Paul, F.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 5373. (b) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
89. 2. See: (a) Paul, F.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 5373. (b) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
90. Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407.
91. Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485.
92. (a) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121.
93. (b) Jeffery, T. Tetrahedron Lett. 1993, 34, 1133.
94. (a) Karabelas, K.; Hallberg, A. Tetrahedron Lett. 1985, 26, 3131.
95. (b) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896.
96. (c) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286.
97. (d) Karabelas, K.; Hallberg, A. J. Org. Chem. 1989, 54, 1773.
98. 4 in olefin insertion, into the palladium-aryl bond, see; Kawataka, F.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 654.
99. AgOTf was also found by Overman's group to be less efficient in the suppression of alkene isomerization, see ref 11a.
100. 3- is weak. In contrast, the interactions between non silver containing monovalent counterions is expected to be stronger. See ref 31a.
101. 3 results in a low displacement energy. Manzer, L. M.; Tolman, C. A. J. Am. Chem. Soc. 1975, 97, 1955.
102. 3. Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
103. Irrespective if the reaction follows a neutral or cationic pathway, olefin 8 is more reactive than 4a. For a more general discussion, see ref 9f.
104. (a) Amino, Y.; Nishi, S.; Izawa, K. Bull. Chem. Soc. Jpn. 1991, 64, 620.
105. (b) Wistrand, L. G. Janssen Chim. Acta, 1986, 4, 34 and references cited therein.
106. (a) Ebenöther, A.; Hasspacher, K. Swiss Patent 526,536, 1972. Chem. Abstr. 1972, 77, 164454s.
107. (b) Bettoni, G.; Cellucci, C.; Tortorella, V. J. Heterocycl. Chem. 1976, 13, 1053.
108. (c) Tseng, C. C.; Terashima, S.; Yamada, S. I. Chem. Pharm. Bull. 1977, 25, 166.
109. (d) Laborde, E. Tetrahedron Lett. 1992, 33, 6607.
110. (e) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36.
111. (f) Adkins, H.; Coonradt, H. J. Am. Chem. Soc. 1941, 63, 1563.
112. Prepared and developed by Prof. W. A. König, Institut für Organische Chemie, Universität Hamburg, D-20146 Hamburg (Germany).
113. Sonesson, C.; Lindborg, J. Tetrahedron Lett. 1994, 35, 9063.
114. Stang, P. J.; Treptow, W. Synthesis 1980, 283.
115. Armande, J. C. L.; Pandit, U. K. Tetrahedron Lett. 1977, 11, 897.
116. Arvidsson, L.-E.; Carlsson, A.; Hacksell, U.; Hjort, S.; Lindberg, P.; Nilsson, L. G.; Sanchez, D.; Svensson, U.; Wikström, H. EP 30526A1, 1981. Chem. Abstr. 96 (1982) 122637r.