Palladium-catalyzed carboetherification and carboamination reactions of γ-hydroxy- and γ-aminoalkenes for the synthesis of tetrahydrofurans and pyrrolidines

European Journal of Organic Chemistry

Volumn , Issue 4, 2007, Pages 571-582

  Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Alcohols; Amines; Electrophilic addition; Heterocycles; Palladium

Indexed keywords

EID: 33846644502     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600767     Document Type: Short Survey

References (86)

1. a) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540;
2. b) M. C. Zafra-Polo, B. Figadere, T. Gallardo, J. R. Tormo, D. Cortes, Phytochemistry 1998, 48, 1087-1117.
3. M. M. Faul, B. E. Huff, Chem. Rev. 2000, 100, 2407-2474.
4. M. Saleem, H. J. Kim, M. S. Ali, Y. S. Lee, Nat. Prod. Rep. 2005, 22, 696-716.
5. E. J. Kang, E. Lee, Chem. Rev. 2005, 105, 4348-4378.
6. a) D. O'Hagen, Nat. Prod. Rep. 2000, 17, 435-446;
7. b) A. Mitchinson, A. Nadin, J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892;
8. c) G. Massiot, C. Delaude, Alkaloids 1986, 27, 269-322.
9. R. G. Powell, D. Weisleder, C. R. Smith Jr., W. K. Rohwedder, Tetrahedron Lett. 1970, 11, 815-818.
10. a) R. E. Schwartz, J. Liesch, O. Hensens, L. Zitano, S. Honeycutt, G. Garrity, R. A. Fromtling, J. Onishi, R. Monaghan, J. Antibiot. 1988, 41, 1774-1779;
11. b) T. V. Achenbach, P. E. Slater, H. Brummerhop, T. Bach, R. Müller, Antimicrob. Agents Chemother. 2000, 44, 2794-2801;
12. c) T. G. Kinzy, J. W. Harger, A. Carr-Schmid, J. Kwon, M. Shastry, M. Justice, J. D. Dinman, Virology 2002, 300, 60-70.
13. a) B. A. Sobin, F. W. Tanner Jr., J. Am. Chem. Soc. 1954, 76, 4053;
14. b) O. Schwardt, U. Veith, C. Gaspard, V. Jäger, Synthesis 1999, 1473-1490.
15. M. Shibano, S. Kitagawa, G. Kusano, Chem. Pharm. Bull. 1997, 45, 505-508.
16. a) T. L. B. Boivin, Tetrahedron 1987, 43, 3309-3362;
17. b) J.-C. Harmange, B. Figadere, Tetrahedron: Asymmetry 1993, 4, 1711-1754;
18. c) M. Pichon, B. Figadere, Tetrahedron: Asymmetry 1996, 7, 927-964;
19. d) J. P. Wolfe, M. B. Hay Tetrahedron 2006, in press.
20. For a recent Microreview that describes the synthesis of tetrahydropyrans, see: P. A. Clarke, S. Santos, Eur. J. Org. Chem. 2006, 2045-2053.
21. For notable exceptions, see: a) K. Mikami, M. Shimizu, Tetrahedron 1996, 52, 7287-7296;
22. b) E. S. Sherman, S. R. Chemler, T. B. Tan, O. Gerlits, Org. Lett. 2004, 6, 1573-1575.
23. M. F. Semmelhack, C. Bodurow, J. Am. Chem. Soc. 1984, 106, 1496-1498.
24. For additional studies in this area, see: a) M. F. Semmelhack, N. Zhang, J. Org. Chem. 1989, 54, 4483-4485;
25. b) M. McCormick, R. Monahan III, J. Soria, D. Goldsmith, D. Liotta, J. Org. Chem. 1989, 54, 4485-4487;
26. c) M. F. Semmelhack, C. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler, M. Meier, Pure Appl. Chem. 1990, 62, 2035-2040;
27. d) Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai, M. Hojo, Z. Yoshida, Tetrahedron Lett. 1985, 26, 3207-3210.
28. M. F. Semmelhack, W. R. Epa, A. W.-H. Cheung, Y. Gu, C. Kim, N. Zhang, W. Lew, J. Am. Chem. Soc. 1994, 116, 7455-7456.
29. a) G. C. Paddon-Jones, N. L. Hungerford, P. Hayes, W. Kitching, Org. Lett. 1999, 1, 1905-1907;
30. b) M. F. Semmelhack, P. Shanmugam, Tetrahedron Lett. 2000, 41, 3567-3571;
31. c) P. Y. Hayes, W. Kitching, J. Am. Chem. Soc. 2002, 124, 9718-9719.
32. G. C. Paddon-Jones, C. S. P. McErlean, P. Hayes, C. J. Moore, W. A. Konig, W. Kitching, J. Org. Chem. 2001, 66, 7487-7495.
33. M. Babjak, P. Kapitan, T. Gracza, Tetrahedron 2005, 61, 2471-2479.
34. a) L. S. Hegedus, G. F. Allen, D. J. Olsen, J. Am. Chem. Soc. 1980, 102, 3583-3587;
35. b) Y. Tamaru, T. Kobayashi, S. Kawamura, H. Ochiai, Z. Yoshida, Tetrahedron Lett. 1985, 26, 4479-4482;
36. c) Y. Tamaru, M. Hojo, H. Higashimura, Z. Yoshida, J. Am. Chem. Soc. 1988, 110, 3994-4002;
37. d) Y. Tamaru, M. Hojo, Z. Yoshida, J. Org. Chem. 1988, 53, 5731-5741;
38. e) H. Harayama, H. Okuno, Y. Takahashi, M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 1996, 37, 7287-7290;
39. f) Y. Tamaru, M. Kimura, Synlett 1997, 749-757;
40. g) H. Harayama, A. Abe, T. Sakado, M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1997, 62, 2113-2122.
41. For related reactions of aminoallenes, see: D. Lathbury, P. Vernon, T. Gallagher, Tetrahedron Lett. 1986, 27, 6009-6012.
42. W.-H. Ham, Y. H. Jung, K. Lee, C.-Y. Oh, K.-Y. Lee, Tetrahedron Lett. 1997, 38, 3247-3248.
43. C.-Y. Oh, K.-S. Kim, W.-H. Ham, Tetrahedron Lett. 1998, 39, 2133-2136.
44. M. F. Semmelhack, W. R. Epa, Tetrahedron Lett. 1993, 34, 7205-7208.
45. a) C. C. Scarborough, S. S. Stahl, Org. Lett. 2006, 8, 3251-3254;
46. 2 that affords a tricyclic pyrrolidine, see: J. L. Brice, J. E. Harang, V. I. Timokhin, N. R. Anastasi, S. S. Stahl, J. Am. Chem. Soc. 2005, 127, 2868-2869.
47. K.-T. Yip, M. Yang, K.-L. Law, N.-Y. Zhu, D. Yang, J. Am. Chem. Soc. 2006, 128, 3130-3131.
48. For related transformations of γ-hydroxy allenes or alkynes see: a) G. Balme, D. Bouyssi, T. Lomberget, N. Monteiro, Synthesis 2003, 2115-2134;
49. b) S.-K. Kang, T.-G. Baik, A. N. Kulak, Synlett 1999, 324-326;
50. c) R. D. Walkup, L. Guan, M. D. Mosher, S. W. Kim, Y. S. Kim, Synlett 1993, 88-90;
51. d) F. T. Luo, I. Schreuder, R. T. Wang, J. Org. Chem. 1992, 57, 2213-2215.
52. a) J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc. 2004, 126, 1620-1621;
53. b) M. B. Hay, A. R. Hardin, J. P. Wolfe, J. Org. Chem. 2005, 70, 3099-3107.
54. 3-catalyzed Heck arylation of an enyne bearing a γ-hydroxy group produced a small amount of a tetrahydrofuran derivative as a minor side product. In our hands, these conditions provided only a trace amount of 2-(2-naphthylmethyl)tetrahydrofuran (36) in the reaction of 4-penten-1-ol with 2-bromonaphthalene. See: B. M. Trost, W. Pfrengle, H. Urabe, J. Dumas, J. Am. Chem. Soc. 1992, 114, 1923-1924.
55. M. B. Hay, J. P. Wolfe, J. Am. Chem. Soc. 2005, 127, 16468-16476.
56. [29].
57. M. B. Hay, J. P. Wolfe, Tetrahedron Lett. 2006, 47, 2793-2796.
58. M.-C. P. Yeh, W.-C. Tsao, L.-H. Tu, Organometallics 2005, 24, 5909-5915.
59. a) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 291, 131-209;
60. b) J. F. Hartwig, in: Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, pp. 107-168.
61. G. Fournet, G. Balme, J. Gore, Tetrahedron 1990, 46, 7763-7774.
62. J. E. Ney, J. P. Wolfe, Angew. Chem. 2004, 116, 3689-3692;
63. Angew. Chem. Int. Ed. 2004, 43, 3605-3608.
64. Small amounts (ca. 1-10%) of 3-aryl-2-methylpyrrolidine regioisomers were generated in these transformations, and are formed through the mechanism described in footnote 30.
65. J. E. Ney, M. B. Hay, Q. Yang, J. P. Wolfe, Adv. Synth. Catal. 2005, 347, 1614-1620.
66. a) R. Lira, J. P. Wolfe, J. Am. Chem. Soc. 2004, 126, 13906-13907;
67. b) Q. Yang, J. E. Ney, J. P. Wolfe, Org. Lett. 2005, 7, 2575-2578.
68. J. E. Ney, J. P. Wolfe, J. Am. Chem. Soc. 2005, 127, 8644-8651.
69. M. B. Bertrand, J. P. Wolfe, Tetrahedron 2005, 61, 6447-6459.
70. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999.
71. M. B. Bertrand, J. P. Wolfe, Org. Lett. 2006, 8, 2353-2356.
72. a) J. H. Johnson, D. W. Phillipson, A. D. Kahle, J. Antibiot. 1989, 42, 1184-1185;
73. b) K. Kasahara, M. Yoshida, J. Eishima, K. Takesako, T. Beppu, S. Horinouchi, J. Antibiot. 1997, 50, 267-269.
74. For a recent review, see: B. Basler, S. Brandes, A. Spiegel, T. Bach, Top. Curr. Chem. 2005, 243, 1-42.
75. a) G. D. Harris Jr., R. J. Herr, S. M. Weinreb, J. Org. Chem. 1992, 57, 2528-2530;
76. b) G. D. Harris Jr., R. J. Herr, S. M. Weinreb, J. Org. Chem. 1993, 58, 5452-5464;
77. c) R. C. Larock, H. Yang, S. M. Weinreb, R. J. Herr, J. Org. Chem. 1994, 59, 4172-4178.
78. a) M. Ukiya, T. Akihisa, K. Yasukawa, Y. Kasahara, Y. Kimura, K. Koike, T. Nikaido, M. Takido, J. Agric. Food Chem. 2001, 49, 3187-3197;
79. b) A. Spinella, E. Mollo, E. Trivellone, G. Cimino, Tetrahedron 1997, 53, 16891-16896;
80. c) H. R. Arthur, P. D. S. Ko, H. T. Cheung, Phytochemistry 1974, 13, 2551-2557.
81. J. S. Nakhla, J. W. Kampf, J. P. Wolfe, J. Am. Chem. Soc. 2006, 128, 2893-2901.
82. a) J. Dumas, Curr. Opin. Drug. Disc. Dev. 2002, 5, 718-727;
83. b) J.-M. Kim, T. E. Wilson, T. C. Norman, P. G. Schultz, Tetrahedron Lett. 1996, 37, 5309-5312;
84. c) W. M. Kazmierski, E. Furfine, Y. Gray-Nunez, A. Spaltenstein, L. Wright, Bioorg. Med Chem. Lett. 2004, 14, 5685-5687.
85. G. Sartori, R. Maggi, in: Science of Synthesis (Houben-Weyl Methods of Molecular Transformations), vol. 18 (Eds.: S. V. Ley, J. G. Knight), Thieme, Stuttgart, 2005, pp. 665-758.
86. J. A. Fritz, J. S. Nakhla, J. P. Wolfe, Org. Lett. 2006, 8, 2531-2534.