Tandem radical-addition-aldol-type reaction of an α,β- unsaturated oxime ether

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6190-6193

  Ueda, Masafumi ^a   Miyabe, Hideto ^b   Sugino, Hisako ^a   Miyata, Okiko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Boranes; Enamines; Oxime ethers; Radical reactions

Indexed keywords

ASYMMETRIC SYNTHESIS; BORANES; ENAMINES; OXIME ETHERS; RADICAL REACTIONS;

ADDITION REACTIONS; ALCOHOLS; AMINO ACIDS; CHEMICAL BONDS; FREE RADICALS; SYNTHESIS (CHEMICAL);

ETHERS;

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; ETHER DERIVATIVE; FORMALDEHYDE; FREE RADICAL; OXIME; PARAFORMALDEHYDE; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ALDEHYDES; ETHERS; FORMALDEHYDE; FREE RADICALS; MOLECULAR STRUCTURE; OXIMES; POLYMERS;

EID: 25844449049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502263     Document Type: Article

References (60)

1. a) P. Renaud, M. Gerster, Angew. Chem. 1998, 110, 2104;
2. Angew. Chem. Int. Ed. 1998, 37, 2562;
3. b) M. P. Sibi, N. A. Porter, Acc. Chem. Res. 1999, 32, 163;
4. c) Radicals in Organic Synthesis, Vols. 1 and 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001;
5. d) M. P. Sibi, S. Manyem, J. Zimmerman, Chem. Rev. 2003, 103, 3263;
6. e) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033.
7. For selected examples of tandem radical allylation, see: a) D. P. Curran, W. Shen, J. Zhang, T. A. Heffnerm, J. Am. Chem. Soc. 1990, 112, 6738;
8. b) B. Giese, M. Zehnder, M. Roth, H.-G. Zeitz, J. Am. Chem. Soc. 1990, 112, 6741;
9. c) N. A. Porter, I. J. Rosenstein, R. A. Breyer, J. D. Bruhnke, W.-X. Wu, A. T. McPhail, J. Am. Chem. Soc. 1992, 114, 7664;
10. d) J. H. Wu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11 029;
11. e) M. P. Sibi, J. Ji, J. Org. Chem. 1996, 61, 6090;
12. f) M. P. Sibi, J. Chen, J. Am. Chem. Soc. 2001, 123, 9472.
13. For selected examples of tandem radical reaction, see: a) D. P. Curran, M.-H. Chen, E. Spletzer, C. M. Seong, C.-T. Chang, J. Am. Chem. Soc. 1989, 111, 8872;
14. b) J. Marco-Contelles, Chem. Commun. 1996, 2629;
15. c) K. Takai, N. Matsukawa, A. Takahashi, T. Fujii, Angew. Chem. 1998, 110, 160;
16. Angew. Chem. Int. Ed. 1998, 37, 152;
17. d) C. Aïssa, A.-L. Dhimane, M. Malacria, Angew. Chem. 2002, 114, 3418;
18. Angew. Chem. Int. Ed. 2002, 41, 3284;
19. e) S. Yamago, M. Miyoshi, H. Miyazoe, J. Yoshida, Angew. Chem. 2002, 114, 1465;
20. Angew. Chem. Int. Ed. 2002, 41, 1407;
21. f) K. Takasu, H. Ohsato, J. Kuroyanagi, M. Ihara, J. Org. Chem. 2002, 67, 6001;
22. g) A. Demircan, P. J. Parsons, Eur. J. Org. Chem. 2003, 1729;
23. h) K. Tsuchii, M. Doi, T. Hirao, A. Ogawa, Angew. Chem. 2003, 115, 3614;
24. Angew. Chem. Int. Ed. 2003, 42, 3490;
25. i) F. Denes, F. Chemla, J. F. Normant, Angew. Chem. 2003, 115, 4177;
26. Angew. Chem. Int. Ed. 2003, 42, 4043;
27. j) K. Miura, M. Tojino, N. Fujisawa, A. Hosomi, I. Ryu, Angew. Chem. 2004, 116, 2477;
28. Angew. Chem. Int. Ed. 2004, 43, 2423;
29. k) M. Tojino, Y. Uenoyama, T. Fukuyama, I. Ryu, Chem. Commun. 2004, 2482;
30. l) Y. Uenoyama, T. Fukuyama, O. Nobuta, H. Matsubara, I. Ryu, Angew. Chem. 2005, 117, 1099;
31. Angew. Chem. Int. Ed. 2005, 44, 1075.
32. a) K. Nozaki, K. Oshima, K. Utimoto, Tetrahedron Lett. 1988, 29, 1041;
33. b) K. Nozaki, K. Oshima, K. Utimoto, Bull. Chem. Soc. Jpn. 1991, 64, 403.
34. a) S. Bazin, L. Feray, D. Siri, J.-V. Naubron, M. P. Bertrand, Chem. Commun. 2002, 2506 ;
35. b) S. Chandrasekhar, C. Narsihmulu, N. R. Reddy, M. S. Reddy, Tetrahedron Lett. 2003, 44, 2583;
36. c) H. Miyabe, R. Asada, K. Yoshida, Y. Takemoto, Synlett 2004, 540;
37. d) Y. Yamamoto, S. Nakano, H. Maekawa, I, Nishiguchi, Org. Lett. 2004, 6, 799;
38. e) S. Bazin, L. Feray, N. Vanthuyne, M. P. Bertrand, Tetrahedron 2005, 61, 4261.
39. a) H. Miyabe, C. Ushiro, T. Naito, Chem. Commun. 1997, 1789;
40. b) H. Miyabe, K. Fujii, T. Naito, Org. Lett. 1999, 1, 569;
41. c) H. Miyabe, C. Ushiro, M. Ueda, K. Yamakawa, T. Naito, J. Org. Chem. 2000, 65, 176;
42. d) H. Miyabe, K. Fujii, T. Naito, Org. Biomol. Chem. 2003, 1, 381;
43. e) M. Ueda, H. Miyabe, H. Sugino, T. Naito, Org. Biomol. Chem. 2005, 3, 1124.
44. a) H. Miyabe, R. Shibata, C. Ushiro, T. Naito, Tetrahedron Lett. 1998, 39, 631;
45. b) H. Miyabe, M. Ueda, N. Yoshioka, T. Naito, Synlett 1999, 465;
46. c) H. Miyabe, M. Ueda, T. Naito, Chem. Commun. 2000, 2059.
47. For reviews, see: a) G. K. Friestad, Tetrahedron 2001, 57, 5461;
48. b) H. Miyabe, M. Ueda, T. Naito, Synlett 2004, 1140.
49. a) M. P. Bertrand, L. Feray, R. Nouguier, L. Stella, Synlett 1998, 780;
50. b) M. P. Bertrand, L. Feray, R. Nouguier, P. Perfetti, J. Org. Chem. 1999, 64, 918;
51. c) M. P. Bertrand, S. Coantic, L. Feray, R. Nouguier, P. Perfetti, Tetrahedron 2000, 56, 3951.
52. a) G. K. Friestad, J. Qin, J. Am. Chem. Soc. 2000, 122, 8329;
53. b) G. K. Friestad, J. Qin, J. Am. Chem. Soc. 2001, 123, 9922;
54. c) G. K. Friestad, Y. Shen, E. L. Ruggles, Angew. Chem. 2003, 115, 5215;
55. Angew. Chem. Int. Ed. 2003, 42, 5061.
56. S. Azam, A. A. D'Souza, P. B. Wyatt, J. Chem. Soc. Perkin Trans. 1 1996, 621.
57. 2. See: I. Ryu, F. Araki, S. Minakata, M. Komatsu, Tetrahedron Lett. 1998, 39, 6335.
58. a) D. S. Tan, M. A. Foley, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073;
59. b) H. T. Openshaw, N. Whittaker, J. Chem. Soc. C 1969, 89.
60. Bahmanyar and Houk reported a theoretical study of the aldol reaction of an enamine with acetaldehyde. Although there are two possible conformations of the six-membered ring transition state involving an equatorial or axial methyl group on acetaldehyde, the two conformations are predicted to be equal in energy. See: S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 11 273.