Rhodium-catalyzed allylation of aldehydes with homoallylic alcohols by retroallylation and isomerization to saturated ketones with conventional or microwave heating

Chemistry - An Asian Journal

Volumn 3, Issue 1, 2008, Pages 119-125

  Sumida, Yuto ^a   Takada, Yuko ^a   Hayashi, Sayuri ^a   Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allylation; C C activation; Isomerization; Retro reactions; Rhodium

Indexed keywords

EID: 40649116007     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700255     Document Type: Article

References (77)

1. a) M. Murakami, Y. Ito in Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, Berlin, 1999, pp. 97-129;
2. b) K. C. Bishop III, Chem. Rev. 1976, 76, 461-486;
3. c) R. H. Crabtree, Chem. Rev. 1985, 85, 245-269;
4. d) B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918-932;
5. Angew. Chem. Int. Ed. 1999, 38, 870-883;
6. e) T. Kondo, T. Mitsudo, Chem. Lett. 2005, 1462-1467;
7. f) C. H. Jun, Chem. Soc. Rev. 2004, 33, 610-618;
8. g) T. Nishimura, S. Uemura, Synlett 2004, 201-216;
9. h) M. Catellani, Synlett 2003, 298-313;
10. i) P. W. Jennings, L. L. Johnson, Chem. Rev. 1994, 94, 2241-2290.
11. For Mg, Li, and Zn, see: a) R. A. Benkeser, W. E. Broxterman, J. Am. Chem. Soc. 1969, 91, 5162-5163;
12. b) R. A. Benkeser, M. P. Siklosi, J. Org. Chem. 1976, 41, 3212-3213;
13. c) R. A. Benkeser, M. P. Siklosi, E. C. Mozdzen, J. Am. Chem. Soc. 1978, 100, 2134-2139;
14. d) P. Miginiac, Bull. Soc. Chim. Fr. 1970, 1077-1083;
15. e) F. Gérard, P. Miginiac, Bull. Soc. Chim. Fr. 1974, 2527-2533;
16. f) F. Barbot, P. Miginiac, J. Organomet. Chem. 1977, 132, 445-454;
17. g) P. Jones, P. Knochel, J. Org. Chem. 1999, 64, 186-195;
18. for Sn, see: h) V. Peruzzo, G. Tagliavini, J. Organomet. Chem. 1978, 162, 37-44;
19. i) A. Yanagisawa, T. Aoki, T. Arai, Synlett 2006, 2071-2074;
20. for Ru, see: j) T. Kondo, K. Kodoi, E. Nishinaga, T. Okada, Y. Morisaki, Y. Watanabe, T. Mitsudo, J. Am. Chem. Soc. 1998, 120, 5587-5588;
21. k) T. Kondo, T. Mitsudo, Chem. Lett. 2005, 1462-1467;
22. for Zr, see: l) K. Fujita, H. Yorimitsu, K. Oshima, Chem. Rec. 2004, 4, 110-119;
23. m) K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima, J. Org. Chem. 2004, 69, 3302-3307;
24. for Ga, see: n) S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2005, 7, 3577-3579;
25. o) S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Organomet. Chem. 2007, 692, 505-513;
26. for Pd, see: p) S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2006, 128, 2210-2211;
27. q) M. Iwasaki, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2007, 129, 4463-4469;
28. r) M. Iwasaki, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Tetrahedron 2007, 63, 5200-5203.
29. a) Y. Takada, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 2515-2517;
30. b) M. Jang, S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, Tetrahedron Lett. 2007, 48, 4003-4005.
31. For rhodium-mediated b-carbon elimination from alkoxy rhodium compounds, see: a) A. Funayama, T. Satoh, M. Miura, J. Am. Chem. Soc. 2005, 127, 15354-15355;
32. b) T. Matsuda, M. Makino, M. Murakami, Org. Lett. 2004, 6, 1257-1259;
33. c) P. Zhao, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 3124-3125;
34. d) T. Nishimura, T. Katoh, T. Hayashi, Angew. Chem. 2007, 119, 5025-5027;
35. Angew. Chem. Int. Ed. 2007, 46, 4937-4939;
36. for the transformation of a homoallyloxy rhodium compound into a π-allyl rhodium compound through carbon-carbon bond cleavage, see: e) P. Zhao, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 9642-9643.
37. a) M. Shi, G.-X. Lei, Y. Masaki, Tetrahedron: Asymmetry 1999, 10, 2071-2074;
38. b) Y. Masuyama, Y. Kaneko, Y. Kurusu, Tetrahedron Lett. 2004, 45, 896-8971.
39. We have adopted the unambiguous erythro/threo nomenclature: R. Noyori, I. Nishida, J. Sakata, J. Am. Chem. Soc. 1981, 103, 2106-2108.
40. For convenience, we define crotylation, methallylation, and prenylation as the addition of a 1-methyl-2-propenyl, 2-methyl-2-propenyl, or 1,1-dimethyl-2-propenyl group, respectively, to a carbonyl group. On the other hand, we refer herein to the crotyl, methallyl, and prenyl groups as the 2-butenyl, 2-methyl-2-propenyl, and 3-methyl-2-butenyl groups, respectively.
41. For the rhodium-catalyzed isomerization of unsaturated alcohols, see: a) R. Uma, C. Crévisy, R. Grée, Chem. Rev. 2003, 103, 27-52;
42. b) M. K. E. Saïah, R. Pellicciari, Tetrahedron Lett. 1995, 36, 4497-4500;
43. c) R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872-2873;
44. d) H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248-3249.
45. For reviews on microwave-assisted organic reactions, see: a) Microwave Assisted Organic Synthesis (Eds.: J. P. Tierney, P. Lidström), Blackwell, Oxford, 2005;
46. b) M. Larhed, K. Olofsson, Microwave Methods in Organic Synthesis, Springer, Berlin, 2006;
47. c) B. A. Roberts, C. R. Strauss, Acc. Chem. Res. 2005, 38, 653-661;
48. d) H. Tokuyama, M. Nakamura, J. Synth. Org. Chem. Jpn. 2005, 63, 523-538;
49. e) A. de La Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164-178;
50. f) C. O. Kappe, Angew. Chem. 2004, 116, 6408-6443;
51. Angew. Chem. Int. Ed. 2004, 43, 6250-6284;
52. g) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283;
53. h) S. Caddick, Tetrahedron 1995, 51, 10 403-10 432;
54. i) D. M. P. Mingos, D. R. Baghurst, Chem. Soc. Rev. 1991, 20, 1-47.
55. G. A. Slough, J. R. Ashbaugh, L. A. Zannoni, Organometallics 1994, 13, 3587-3593.
56. a) S. Garbacia, B. Desai, O. Lavastre, C. O. Kappe, J. Org. Chem. 2003, 68, 9136-9139;
57. b) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223;
58. c) N. Kuhnert, Angew. Chem. 2002, 114, 1943-1946;
59. Angew. Chem. Int. Ed. 2002, 41, 1863-1866;
60. d) C. R. Strauss, Angew. Chem. 2002, 114, 3741-3743;
61. Angew. Chem. Int. Ed. 2002, 41, 3589-3590.
62. J.-S. Shiue, M.-H. Lin, J.-M. Fang, J. Org. Chem. 1997, 62, 4643-4649.
63. T. Ishiyama, H. Kizaki, T. Hayashi, A. Suzuki, N. Miyaura, J. Org. Chem. 1998, 63, 4726-4731.
64. M. A. Al-Aseer, S. G. Smith, J. Org. Chem. 1984, 49, 2608-2613.
65. S. Kobayashi, K. Nishio, J. Org. Chem. 1994, 59, 6620-6628.
66. I. Shibata, N. Yoshimura, M. Yabu, A. Baba, Eur. J. Org. Chem. 2001, 3207-3211.
67. For the syn isomer, see: S. E. Denmark, J. Fu, J. Am. Chem. Soc. 1992, 114, 2577-2586;
68. for the anti isomer, see: A. V. Malkov, L. Dufková, L. Farrugia, P. Kocovsky, Angew. Chem. 2003, 115, 3802-3805;
69. Angew. Chem. Int. Ed. 2003, 42, 3674-3677.
70. J. Takahara, Y. Masuyama, Y. Kurusu, J. Am. Chem. Soc. 1992, 114, 2577-2586.
71. M. Ito, S. Kitahara, T. Ikariya, J. Am. Chem. Soc. 2005, 127, 6172-6173.
72. S. W. Lee, K. Lee, D. Seomoon, S. Kim, H. Kim, H. Kim, E. Shim, M. Lee, S. Lee, M. Kim, P. H. Lee, J. Org. Chem. 2004, 69, 4852-4855.
73. S. R. Stauffer, C. J. Coletta, R. Tedesco, G. Nishiguchi, K. Carlson, J. Sun, B. S. Katzenellenbogen, J. A. Katzenellenbogen, J. Med. Chem. 2000, 43, 4943-4947.
74. F. A. Luzzio, R. W. Fitch, J. Prakt. Chem. 2000, 342, 498-501.
75. I. Fleming, A. J. Lawrence, R. D. Richardson, D. S. Surry, M. C. West, Helv. Chim. Acta 2002, 85, 3349-3365.
76. P. Kraft, K. Popaj, Tetrahedron 2006, 62, 12 211-12 219.
77. A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 14800-14801.