Gold-catalyzed cycloisomerization of α-aminoallenes to 3-pyrrolines - Optimization and mechanistic studies

European Journal of Organic Chemistry

Volumn , Issue 20, 2006, Pages 4634-4641

  Morita, Nobuyoshi ^a,b   Krause, Norbert ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Aminoallenes; 3 Pyrrolines; Chirality transfer; Cycloisomerization; Gold; Heterocycles; Homogeneous catalysis; Intramolecular hydroamination

Indexed keywords

EID: 33750410941     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600438     Document Type: Article

References (75)

1. a) S. G. Pyne, A. S. Davis, N. J. Gates, J. P. Hartley, K. B. Lindsay, T. Machan, M. Tang, Synlett 2004, 2670-2680;
2. b) D. Enders, C. Thiebes, Pure Appl. Chem. 2001, 73, 573-578;
3. c) D. O'Hagen, Nat. Prod Rep. 2000, 17, 435-446;
4. d) A. B. Mauger, J. Nat. Prod. 1996, 59, 1205-1211;
5. e) C. M. Huwe, S. Blechert, Tetrahedron Lett. 1995, 36, 1621-1624.
6. 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;
7. b) J. H. Johnson, D. W. Phillipson, A. D. Kahle, J. Antibiot. 1989, 42, 1184-1185;
8. c) A. N. Hulme, E. M. Rosser, Org. Lett. 2002, 4, 265-267;
9. d) M. Overhand, S. M. Hecht, J. Org. Chem. 1994, 59, 4721-4722;
10. e) W. Deng, L. E. Overman, J. Am. Chem. Soc. 1994, 116, 11241-11250;
11. f) P. L. McGrane, T. Livinghouse, J. Am. Chem. Soc. 1993, 115, 11485-11489;
12. g) C. S. Pak, G. H. Lee, J. Org. Chem. 1991, 56, 1128-1133.
13. a) A. Toyao, O. Tamura, H. Takagi, H. Ishibashi, Synlett 2003, 35-38;
14. b) E. A. Severino, C. R. D. Correia, Org. Lett. 2000, 2, 3039-3042;
15. c) H. Yoda, T. Nakajima, K. Takabe, Tetrahedron Lett. 1996, 37, 5531-5534;
16. d) C.-H. J. Wang, J. C. Calabrese, J. Org. Chem. 1991, 56, 4341-4343;
17. e) H. Iida, N. Yamazaki, C. Kibayashi, J. Org. Chem. 1987, 52, 1956-1962.
18. a) I. Pastuszak, R. J. Molyneux, L. F. James, A. D. Elbein, Biochemistry 1990, 29, 1886-1891;
19. b) K. L. Chandra, M. Chandrasekhar, V. K. Singh, J. Org. Chem. 2002, 67, 4630-4633;
20. c) A. Brandi, S. Cicchi, F. M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806-6812;
21. d) R. Giovannini, E. Marcantoni, M. Petrini, J. Org. Chem. 1995, 60, 5706-5707.
22. a) C. H. Williams, J. Lawson, Neurobiology 1999, 7, 225-233;
23. b) C. H. Williams, J. Lawson, Biochem. J. 1998, 336, 63-67;
24. c) Y. Lee, H. Huang, L. M. Sayre, J. Am. Chem. Soc. 1996, 118, 7241-7242.
25. D. Rondeau, P. Gill, M. Chan, K. Curry, W. D. Lubell, Bioorg. Med. Chem. Lett. 2000, 10, 771-773.
26. Q.-Y. Mou, J. Chen, Y.-C. Zhu, D.-H. Zhou, Z.-Q. Chi, Y.-Q. Long, Bioorg. Med. Chem. Lett. 2002, 12, 2287-2290.
27. W. K. Anderson, A. S. Milowsky, J. Med. Chem. 1987, 30, 2144-2147.
28. a) S. Ma, F. Yu, W. Gao, J. Org. Chem. 2003, 68, 5943-5949;
29. b) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511-514;
30. c) W. F. J. Karstens, D. Klomp, F. P. J. T. Rutjes, H. Hiemstra, Tetrahedron 2001, 57, 5123-5130;
31. d) H. Ohno, A. Toda, Y. Miwa, T. Taga, E. Osawa, Y. Yamaoka, N. Fujii, T. Ibuka, J. Org. Chem. 1999, 64, 2992-2993;
32. e) W. F. J. Karstens, F. P. J. T. Rutjes, H. Hiemstra, Tetrahedron Lett. 1997, 38, 6275-6278;
33. f) I. W. Davis, D. I. Scopes, T. Gallagher, Synlett 1993, 85-87;
34. g) M. Kimura, K. Fugami, S. Tanaka, Y. Tamaru, J. Org. Chem. 1992, 57, 6377-6379;
35. h) J. S. Prasad, L. S. Liebeskind, Tetrahedron Lett. 1988, 29, 4257-4260.
36. a) R. K. Dieter, N. Chen, H. Yu, L. E. Nice, V. K. Gore, J. Org. Chem. 2005, 70, 2109-2119;
37. b) R. K. Dieter, H. Yu, Org. Lett. 2001, 3, 3855-3858;
38. c) J. D. Ha, J. Cha, J. Am. Chem. Soc. 1999, 121, 10012-10020;
39. d) M. O. Amombo, A. Hausherr, H.-U. Reissig, Synlett 1999, 1871-1874;
40. e) J. D. Ha, D. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 4550-4551;
41. f) W. Davis, I. T. Gallagher, R. B. Lamont, I. C. Scopes, J. Chem. Soc., Chem. Commun. 1992, 335-337;
42. g) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc., Chem. Commun. 1987, 243-244.
43. D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molly, T. Gallagher, J. Chem. Soc., Chem. Commun. 1989, 1073-1075.
44. a) V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633-3639;
45. b) V. M. Arredondo, F. E. McDonald, T. J. Marks, Organometallics 1999, 18, 1949-1960;
46. c) V. M. Arrendondo, F. E. Mcdonald, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 4871-4872.
47. Recent review on homogeneous gold catalysis: a) A. Arcadi, S. Di Giuseppe, Curr. Org. Chem. 2004, 8, 795-812;
48. b) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387-391;
49. c) A. S. K. Hashmi, Angew. Chem. 2005, 117, 7150-7154;
50. Angew. Chem. Int. Ed. 2005, 44, 6990-6993.
51. a) A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538;
52. b) N. Krause, A. Hoffmann-Röder, J. Canisius, Synthesis 2002, 1759-1774.
53. N. Morita, N. Krause, Angew. Chem. 2006, 118, 1930-1933;
54. Angew. Chem. Int. Ed. 2006, 45, 1897-1899.
55. N. Morita, N. Krause, Org. Lett. 2004, 6, 4121-4123.
56. See also: P. H. Lee, H. Kim, K. Lee, M. Kim, K. Noh, H. Kim, D. Seomoon, Angew. Chem. 2005, 117, 1874-1877;
57. Angew. Chem. Int. Ed. 2005, 44, 1840-1843.
58. For other gold-catalyzed intramolecular hydroamination reactions, see: a) Y. Fukuda, K. Utimoto, Synthesis 1991, 975-978;
59. b) X. Han, R. A. Widenhoefer, Angew. Chem. 2006, 118, 1779-1781;
60. Angew. Chem. Int. Ed. 2006, 45, 1747-1749;
61. c) N. T. Patil, L. M. Lutete, N. Nishina, Y. Yamamoto, Tetrahedron Lett. 2006, 47, 4749-4751;
62. d) gold-catalyzed intermolecular hydroamination of allenes: N. Nishina, Y. Yamamoto, Angew. Chem. 2006, 118, 3392-3395;
63. Angew. Chem. Int. Ed. 2006, 45, 3314-3317.
64. Recent examples for the oxidation of 3-pyrrolines to pyrroles: a) B. Clique, C. Anselme, D. Otto, N. Monteiro, G. Balme, Tetrahedron Lett. 2004, 45, 1195-1197;
65. b) K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, J. Am. Chem. Soc. 2004, 126, 5192-5201;
66. c) S. Gowrisankar, K. Y. Lee, J. N. Kim, Tetrahedron Lett. 2005, 46, 4859-4863.
67. W. R. Roush, J. A. Straud, R. T. Brown, J. Org. Chem. 1987, 52, 5127-5136.
68. a) C. Nieto-Oberhuber, S. Lopez, M. P. Munoz, D. J. Cardenas, E. Bunuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304;
69. Angew. Chem. Int. Ed. 2005, 44, 6146-6148;
70. b) C. Nieto-Oberhuber, M. P. Munoz, S. Lopez, E. Jimenez-Nunez, C. Nevado, E. Herrero-Gomez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677-1693.
71. 3.
72. [19b]
73. A. S. K. Hashmi, L. Schwarz, J.-K. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385;
74. Angew. Chem. Int. Ed. 2000, 39, 2285-2288.
75. This view is at variance with a recently published paper on the catalytically active species in the gold-catalyzed cycloisomerization of α-hydroxyallenes:A. S. K. Hashmi, M. C. Blanco, D. Fischer, J. W. Bats, Eur. J. Org. Chem. 2006, 1387-1389.