Chiral amidophosphane-copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes

Tetrahedron

Volumn 61, Issue 31, 2005, Pages 7420-7424

  Valleix, Fanny ^a   Nagai, Kazushige ^a   Soeta, Takahiro ^a   Kuriyama, Masami ^a   Yamada, Ken Ichi ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric reaction; Conjugate addition; Nitroolefin; Organocopper

Indexed keywords

ALKENE DERIVATIVE; COPPER; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 21744436465     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.070     Document Type: Article

References (55)

1. Reviews on enantioselective conjugate addition: (a) K. Tomioka Synthesis 1990 541 549
2. (b) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999.
3. K. Tomioka J. Otera Modern Carbonyl Chemistry 2000 Wiley-VCH Weinheim Chapter 12
4. B.L. Feringa Acc. Chem. Res. 33 2000 346 353
5. M.P. Sibi, and S. Manyem Tetrahedron 56 2000 8033 8061
6. N. Krause, and A. Hoffmann-Röder Synthesis 2001 171 196
7. T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829 2844
8. K. Tomioka E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 2004 Springer New York 109 124 Supplement to Chapter 31.1
9. P. Permulter J.E. Baldwin P.D. Magnus Conjugate Addition Reactions in Organic Synthesis Tetrahedron Organic Chemistry Series Vol 9 1992 Pergamon Oxford
10. A. Alexakis, and C. Benhaim Eur. J. Org. Chem. 2002 3221 3236 and references therein
11. L. Liang, T.T.-L. Au-Yeung, and A.S.C. Chan Org. Lett. 4 2002 3799 3801
12. R. Shintani, and G.C. Fu Org. Lett. 4 2002 3699 3702
13. Y. Hu, X. Liang, J. Wang, Z. Zheng, and X. Hu Tetrahedron: Asymmetry 2003 3907 3915
14. I.J. Krauss, and J.L. Leighton Org. Lett. 5 2003 3201 3203
15. T. Morimoto, N. Mochizuki, and M. Suzuki Tetrahedron Lett. 45 2004 5717 5722
16. A. Alexakis, D. Polet, S. Rosset, and S. March J. Org. Chem. 69 2004 5660 5667
17. A.G.M. Barrett, and G.G. Graboski Chem. Rev. 86 1986 751 762
18. S.E. Denmark, and L.R. Marcin J. Org. Chem. 58 1993 3850 3856
19. G. Kumaran, and G.H. Kulkarni Synthesis 1995 1545
20. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH New York
21. A. Alexakis, and C. Benhaim Org. Lett. 2 2000 2579 2581
22. A. Duursma, A.J. Minnaard, and B.L. Feringa Tetrahedron 58 2002 5773 5778
23. A. Alexakis, D. Polet, S. Rosset, and S. March J. Org. Chem. 69 2004 5660 5667
24. H. Choi, Z. Hua, and I. Ojima Org. Lett. 6 2004 2689 2691
25. S. Ongeri, U. Piarulli, R.F.W. Jackson, and C. Gennari Eur. J. Org. Chem. 2001 803 807
26. J. Kang, J. Lee, and D. Lim Tetrahedron: Asymmetry 14 2003 305 315
27. C.A. Luchaco-Cullis, and A.H. Hoveyda J. Am. Chem. Soc. 124 2002 8192 8193
28. D.M. Mampreian, and A.H. Hoveyda Org. Lett. 6 2004 2829 2832
29. M. Kanai, K. Koga, and K. Tomioka Tetrahedron Lett. 33 1992 7193 7196
30. M. Kanai, K. Koga, and K. Tomioka J. Chem. Soc., Chem. Commun. 1993 1248 1249
31. M. Kanai, and K. Tomioka Tetrahedron Lett. 35 1994 895 898
32. M. Kanai, and K. Tomioka Tetrahedron Lett. 36 1995 4273 4274
33. M. Kanai, and K. Tomioka Tetrahedron Lett. 36 1995 4275 4278
34. Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka Tetrahedron Lett. 37 1996 7805 7808
35. Y. Nakagawa, M. Kanai, Y. Nagaoka, and K. Tomioka Tetrahedron 54 1998 10295 10307
36. M. Kanai, Y. Nakagawa, and K. Tomioka Tetrahedron 55 1999 3831 3842
37. M. Kanai, Y. Nakagawa, and K. Tomioka Tetrahedron 55 1999 3843 3854
38. Y. Nakagawa, K. Matsumoto, and K. Tomioka Tetrahedron 56 2000 2857 2863
39. H. Fujihara, K. Nagai, and K. Tomioka J. Am. Chem. Soc. 122 2000 12055 12056
40. K. Nagai, H. Fujihara, M. Kuriyama, K. Yamada, and K. Tomioka Chem. Lett. 2002 8 9
41. T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, and K. Tomioka J. Org. Chem. 68 2003 9723 9727
42. T. Soeta, M. Kuriyama, and K. Tomioka J. Org. Chem. 70 2004 297 300
43. T. Mori, K. Kosaka, Y. Nakagawa, Y. Nagaoka, and K. Tomioka Tetrahedron: Asymmetry 9 1998 3175 3178
44. Our other approaches to asymmetric conjugate addition to nitroolefins. (a) M. Yamashita, K. Yamada, and K. Tomioka J. Am. Chem. Soc. 126 2004 1945 1946
45. M. Yamashita, K. Yamada, and K. Tomioka Tetrahedron 60 2004 4237 4242
46. Our other approaches to asymmetric conjugate addition to activated olefins. (a) K. Tomioka, M. Shindo, and K. Koga J. Am. Chem. Soc. 111 1989 8266 8268
47. M. Shindo, K. Koga, and K. Tomioka J. Am. Chem. Soc. 114 1992 8732 8733
48. M. Shindo, K. Koga, and K. Tomioka J. Org. Chem. 63 1998 9351 9357
49. M. Kuriyama, K. Nagai, K. Yamada, Y. Miwa, T. Taga, and K. Tomioka J. Am. Chem. Soc. 124 2002 8932 8939
50. H. Doi, T. Sakai, M. Iguchi, K. Yamada, and K. Tomioka J. Am. Chem. Soc. 125 2003 2886 2887
51. M. Kuriyama, T. Soeta, X. Hao, Q. Chen, and K. Tomioka J. Am. Chem. Soc. 126 2004 8128 8129
52. A. Alexakis, C. Benhaim, S. Rosset, and M. Humam J. Am. Chem. Soc. 124 2002 5262 5263
53. H. Ohta, N. Kobayashi, and K. Ozaki J. Org. Chem. 54 1989 1802 1804
54. M. Schöfer, and D. Seebach Tetrahedron 51 1995 2305 2324
55. P. Jones, C.K. Reddy, and P. Knochel Tetrahedron 54 1998 1471 1490