Rhodium-catalyzed regio-, diastereo-, and enantioselective intermolecular [4+2] carbocyclization of 4-alkynals with electron-deficient alkenes

European Journal of Organic Chemistry

Volumn , Issue 16, 2006, Pages 3582-3595

  Tanaka, Ken ^a   Hagiwara, Yuji ^a   Hirano, Masao ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Aldehydes; Alkenes; Alkynes; Asymmetric catalysis; Carbocyclization; Rhodium

Indexed keywords

EID: 33748353192     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600383     Document Type: Article

References (89)

1. For reviews of transition-metal-catalyzed carbocyclizations, see: a) I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, Chem. Rev. 1996, 96, 635-662;
2. b) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
3. c) P. A. Wender, J. A. Love, in: Advances in Cycloaddition, JAI Press: Greenwich, 1999, vol. 5, p. 1-45;
4. d) J. E. Robinson, in: Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, 2005, p. 241.
5. For transition-metal-catalyzed intramolecular [4+2] carbocyclizations. For Rh, see: a) D. Motoda, H. Kinoshita, H. Shinokubo, K. Oshima, Angew. Chem. 2004, 116, 1896-1898;
6. Angew. Chem. Int. Ed. 2004, 43, 1860-1862;
7. b) B. Wang, P. Cao, X. Zhang, Tetrahedron Lett. 2000, 41, 8041-8044;
8. c) S. R. Gilbertson, G. S. Hoge, Tetrahedron Lett. 1998, 39, 2075-2078;
9. d) P. A. Wender, T. E. Jenkins, S. Suzuki, J. Am. Chem. Soc. 1995, 117, 1843-1844;
10. e) D. J. R. O'Mahony, D. B. Belanger, T. Livinghouse, Org. Biomol. Chem. 2003, 1, 2038-2040;
11. f) R. S. Jolly, G. Luedtke, D. Sheehan, T. Livinghouse, J. Am. Chem. Soc. 1990, 112, 4965-4966;
12. g) M. Murakami, M. Ubukata, K. Itami, Y. Ito, Angew. Chem. 1998, 110, 2362-2364;
13. Angew. Chem. Int. Ed. 1998, 37, 2248-2250;
14. h) B. Witulski, J. Lumtscher, U. Bergsträßer, Synlett 2003, 708-710.
15. For Ni, see; i) P. A. Wender, T. E. Smith, Tetrahedron 1998, 54, 1255-1275;
16. j) P. A. Wender, T. E. Smith, J. Org. Chem. 1996, 61, 824-825;
17. k) P. A. Wender, T. E. Smith, J. Org. Chem. 1995, 60, 2962-2963;
18. l) P. A. Wender, T. E. Jenkins, J. Am. Chem. Soc. 1989, 111, 6432-6434.
19. For Pd, see; m) J. R. Dunetz, R. L. Danheiser, J. Am. Chem. Soc. 2005, 127, 5776-5777;
20. n) L. J. van Boxtel, S. Körbe, M. Noltemeyer, A. de Meijere, Eur. J. Org. Chem. 2001, 2283-2292;
21. o) M. Murakami, K. Itami, Y. Ito, J. Am. Chem. Soc. 1997, 119, 7163-7164;
22. p) K. Kumar, R. Jolly, Tetrahedron Lett. 1998, 39, 3047-3048;
23. q) T. Mandai, S. Suzuki, A. Ikawa, T. Murakami, M. Kawada, J. Tsuji, Tetrahedron Lett. 1991, 32, 7687-7688.
24. For Co, see; r) G. Hilt, S. Lüers, K. I. Smolko, Org. Lett. 2005, 7, 251-253;
25. s) G. Hilt, S. Lüers, K. Harms, J. Org. Chem. 2004, 69, 624-630;
26. t) G. Hilt, K. I. Smolko, Angew. Chem. 2003, 115, 2901-2903;
27. Angew. Chem. Int. Ed. 2003, 42, 2795-2797;
28. u) G. Hilt, L. Steffen, Synthesis 2002, 686-692;
29. v) G. Hilt, S. Lüers, Synthesis 2003, 1784-1786;
30. w) G. Hilt, K. I. Smolko, B. V. Lotsch, Synlett 2002, 1081-1084;
31. x) G. Hilt, T J. Korn, Tetrahedron Lett. 2001, 42, 2783-2785;
32. y) G. Hilt, F. du Mesnil, Tetrahedron Lett. 2000, 41, 6757-6761.
33. For Au, see; z) C. Nietro-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
34. For transition-metal-catalyzed intermolecular [4+2] carbocyclizations, see: a) S.-J. Paik, S. U. Son, Y. K. Chung, Org. Lett. 1999, 1, 2045-2047;
35. b) I. Matsuda, M. Shibata, S. Sato, Y. Izumi, Tetrahedron Lett. 1987, 28, 3361-3362;
36. c) K. Mach, H. Antropiusovä, L. Petrusovä, F. Turecek, V. Hanus, J. Organomet. Chem. 1985, 289, 331-339;
37. d) H. tom Dieck, R. Diercks, Angew. Chem. 1983, 95, 801-802;
38. Angew. Chem. Int. Ed. Engl. 1983, 22, 778-779.
39. For transition-metal-catalyzed enantioselective intramolecular [4+2] carbocyclizations, see: a) T. Shibata, K. Takasaku, Y. Takesue, N. Hirata, K. Takagi, Synlett 2002, 1681-1682;
40. b) H. Heath, B. Wolfe, T. Livinghouse, S. K. Bae, Synthesis 2001, 2341-2347;
41. c) S. R. Gilbertson, G. S. Hoge, D. G. Genov, J. Org. Chem. 1998, 63, 10077-10080;
42. d) D. J. R. O'Mahony, D. B. Belanger, T. Livinghouse, Synlett 1998, 443-445;
43. e) L. Mckinstry, T. Livinghouse, Tetrahedron 1994, 50, 6145-6154.
44. Murakami, Ito, and co-workers reported that the palladium-catalyzed enantioselective intermolecular [4+2] carbocyclization of vinylallenes with 1,3-dienes affords the optically active cyclohexenones with 63-89% ee, see: M. Murakami, R. Minamida, K. Itami, M. Sawamura, Y. Ito, Chem. Commun. 2000, 2293-2294.
45. For synthesis of quinones through reactions of maleoylcobalt complexes with alkynes, see: a) S. Iyer, L. S. Liebeskind, J. Am. Chem. Soc. 1987, 109, 2759-2770;
46. b) L. S. Liebeskind, S. L. Baysdon, V. Goedken, R. Chidambaram, Organometallics 1986, 5, 1086-1092;
47. c) L. S. Liebeskind, J. P. Leeds, S. L. Baysdon, S. Iyer, J. Am. Chem. Soc. 1984, 106, 6451-6453.
48. a) M. Murakami, T. Itahashi, Y. Ito, J. Am. Chem. Soc. 2002, 124, 13976-13977;
49. b) T. Matsuda, A. Fujimoto, M. Ishibashi, M. Murakami, Chem. Lett. 2004, 33, 876-877.
50. K. Tanaka, G. C. Fu, Org. Lett. 2002, 4, 933-935.
51. Preliminary results have been reported: K. Tanaka, Y. Hagiwara, K. Noguchi, Angew. Chem. 2005, 117, 7426-7429;
52. Angew. Chem. Int. Ed. 2005, 44, 7260-7263.
53. Rhodium-catalyzed intramolecular trans hydroacylation of 4-alkynals, see: a) K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 11492-11493;
54. b) K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 10296-10297;
55. c) K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 8078-8079.
56. K. Tanaka, G. C. Fu, Chem. Commun. 2002, 684-685.
57. The reaction of 3-phenyl-5-trimethylsilyl-4-pentynal was conducted at lower temperature (8°C) to minimize the formation of dienal.
58. For these cycloadditions in Table 2, the regioisomers have been easily separated by silica gel chromatography except Entry 6.
59. Cyclopentenone 5b was isolated in 29% yield as a major by-product.
60. T. Sturm, W. Weissensteiner, F. Spindler, Adv. Synth. Catal. 2003, 345, 160-164.
61. 1NMR analyses of the crude reaction mixtures.
62. Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437-3444.
63. For rhodium-catalyzed [4+2] dimerization of 2-vinylbenzaldehyde, see: K. Kundu, J. V. McCullagh, A. T. Morehead Jr, J. Am. Chem. Soc. 2005, 127, 16042-16043.
64. For mechanistic studies of the rhodium-catalyzed cyclization of 4-alkenals to cyclopentanones, see: a) D. P. Fairlie, B. Bosnich, Organometallics 1988, 7, 946-954;
65. b) R. E. Campbell Jr, R. G. Miller, J. Organomet. Chem. 1980, 186, C27-C31;
66. c) R. E. Campbell Jr, C. F. Lochow, K. P. Vora, R. G. Miller, J. Am. Chem. Soc. 1980, 102, 5824-5830.
67. K. Tanaka, G. C. Fu, Angew. Chem. 2002, 114, 1677-1679;
68. Angew. Chem. Int. Ed. 2002, 41, 1607-1609.
69. Rhodium-catalyzed chelation-controlled intermolecular hydroacylation of aldehydes with alkenes, see: a) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. 2004, 116, 344-347;
70. Angew. Chem. Int. Ed. 2004, 43, 340-343;
71. b) M. Tanaka, M. Imai, Y. Yamamoto, K. Tanaka, M. Shimowatari, S. Nagumo, N. Kawahara, H. Suemune, Org. Lett. 2003, 5, 1365-1367;
72. c) C.-H. Jun, C. W. Moon, D.-Y. Lee, Chem. Eur. J. 2002, 8, 2423-2428.
73. M. Eriksson, T. Iliefski, M. Nilsson, T. Olsson, J. Org. Chem. 1997, 62, 182-187.
74. K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86-94.
75. L. Brandsma, H. D. Verkruijsse, Recl. Trav. Chim. Pays-Bas 1974, 93, 319-320.
76. C. R. Harris, S. D. Kuduk, A. Balog, K. Savin, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 7050-7062.
77. J. W. Herndon, J. J. Matasi, J. Org. Chem. 1990, 55, 786-788.
78. N. Asao, T. Nogami, K. Takahashi, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 764-765.
79. A. V. R. Rao, S. Krishnappa, K. L. N. Reddy, K. A. Reddy, Synth. Commun. 1986, 16, 1141-1148.
80. T. Honda, M. Hoshi, K. Kanai, M. Tsubuki, J. Chem. Soc., Perkin Trans. 1 1994, 15, 2091-2101.
81. T. C. Bedard, J. S. Moore, J. Am. Chem. Soc. 1995, 117, 10662-10671.
82. T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806-3807.
83. Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437-3444.
84. P. Sagar, R. Fröhlich, E.-U. Würthwein, Angew. Chem. Int. Ed. 2004, 43, 5694-5697.
85. J. Barluenga, H. Vazquez-Villa, A. Ballesteros, J. M. Gonzalez, J. Am. Chem. Soc. 2003, 125, 9028-9029.
86. T. Shono, J. Am. Chem. Soc. 1979, 101, 984-987.
87. A. Pouilhés, S. E. Thomas, Tetrahedron Lett. 1989, 30, 2285-2288.
88. K. Tanaka, Y. Hagiwara, M. Hirano, Angew. Chem. 2006, 118, 2800-2803;
89. Angew. Chem. Int. Ed. 2006, 45, 2734-2737.