Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones using a novel N,N,P-Cu(II) complex

Tetrahedron Asymmetry

Volumn 23, Issue 13, 2012, Pages 959-964

  Ebisu, Yasuhiro ^a   Kawamura, Kenjiro ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; COPPER COMPLEX; COPPER DERIVATIVE; KETONE DERIVATIVE; LIGAND; NITROGEN; ORGANOFLUORINE DERIVATIVE; PHOSPHORUS; PYRIDINE; TRIDENTATE LIGAND; TRIFLUOROMETHANESULFONATE COPPER; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

1,4 CYCLOADDITION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; CYCLOADDITION; ENANTIOSELECTIVITY; MOLECULAR WEIGHT; PHASE TRANSITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84864647629     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.06.010     Document Type: Article

References (73)

1. P. Perlmutter Conjugate Addition Reaction in Organic Synthesis In Tetrahedron Organic Chemistry Series Vol. 9 1992 Pergamon Press Oxford
2. K. Tomioka, and Y. Nagaoka E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis 1999 Springer Verlag Berlin, Heidelberg Chapter 31.1
3. K. Tomioka E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis 2004 Springer Verlag Berlin, Heidelberg, New York Supplement to Chapter 31.1
4. A. Alexakis, J. Frutos, and P. Mangeney Tetrahedron: Asymmetry 4 1993 2427
5. For a review: A. Alexakis, and C. Benhaim Eur. J. Org. Chem. 2002 3221
6. M. Kotora, and R. Betík A. Córdova, Catalytic Asymmetric Conjugate Reactions 2010 Wiley-VCH Chapter 2
7. T. Jerphagnon, M.G. Pizzuti, A.J. Minnaard, and B.L. Feringa Chem. Soc. Rev. 38 2009 1039
8. A. Alexakis, J.E. Bäckvall, N. Krause, O. Pàmies, and M. Diéguez Chem. Rev. 108 2008 2796
9. Phosphate ligand: A. Alexakis, J. Vastra, J. Burton, and P. Mangeney Tetrahedron: Asymmetry 8 1997 3193
10. M. Yan, L.-W. Yang, K.Y. Wong, and A.S.C. Chan Chem. Commun. 1999 11
11. M. Yan, Z.-Y. Zhou, and A.S.C. Chan Chem. Commun. 2000 115
12. I.H. Escher, and A. Pfaltz Tetrahedron 56 2000 2879
13. R. Shintani, and G.C. Fu Org. Lett. 4 2002 3699
14. L. Liang, T.T.-L. Au-Yeung, and A.S.C. Chan Org. Lett. 4 2002 3799
15. I.J. Krauss, and J.L. Leighton Org. Lett. 5 2003 3201
16. P. Scafato, S. Labano, G. Cunsolo, and C. Rosini Tetrahedron: Asymmetry 14 2003 3873
17. A. Iuliano, and P. Scafato Tetrahedron: Asymmetry 14 2003 611
18. A. Iuliano, P. Scafato, and R. Torchia Tetrahedron: Asymmetry 15 2004 2533
19. L. Liang, M. Yan, Y.-M. Li, and A.S.C. Chan Tetrahedron: Asymmetry 15 2004 2575
20. L. Wang, Li, C.-W. Yip, L. Qiu, Z. Zhou, and A.S.C. Chan Adv. Synth. Catal. 346 2004 947
21. N. Fuchs, M. D'Augustin, M. Human, A. Alexakis, R. Teras, and S. Gladiali Tetrahedron: Asymmetry 16 2005 3143
22. N. Cramer, S. Laschat, and A. Baro Organometallics 25 2006 2284
23. A. Hajra, N. Yoshikai, and E. Nakamura Org. Lett. 8 2006 4153
24. S. Facchetti, D. Losi, and A. Iuliano Tetrahedron: Asymmetry 17 2006 2993
25. Y. Mata, M. Dieguez, O. Pamies, K. Biswas, and S. Woodward Tetrahedron: Asymmetry 18 2007 1613
26. Q.L. Zhao, L.-L. Wang, F.Y. Kwong, and A.S.C. Chan Tetrahedron: Asymmetry 18 2007 1899
27. A.J. Smith, L.K. Abbot, and S.F. Martin Org. Lett. 11 2009 4200
28. A.H.M. de Vries, A. Meetsma, and B.L. Feringa Angew. Chem., Int. Ed. 35 1996 2374
29. B.L. Feringa, M. Pineschi, L.A. Arnold, R. Imbos, and A.H.M. de Vries Angew. Chem., Int. Ed. 36 1997 2620
30. A. Mandoli, M. Calamante, B.L. Feringa, and P. Salvadori Tetrahedron: Asymmetry 14 2003 3647
31. F. Boeda, D. Rix, H. Clavier, C. Crévisy, and M. Mauduit Tetrahedron: Asymmetry 17 2006 2726
32. X. Hu, H. Chen, and X. Zhang Angew. Chem., Int. Ed. 38 1999 3518
33. Y. Liang, S. Gao, H. Wan, Y. Hu, H. Chen, Z. Zheng, and X. Hu Tetrahedron: Asymmetry 14 2003 3211
34. L.-T. Liu, M.-C. Wang, W.-X. Zhao, Y.-L. Zhou, and X.-D. Wang Tetrahedron: Asymmetry 17 2006 136
35. S.J. Degrado, H. Mizutani, and A.H. Hoveyda J. Am. Chem. Soc. 123 2001 755
36. H. Mizutani, S.J. Degrado, and A.H. Hoveyda J. Am. Chem. Soc. 124 2002 779
37. S.J. Degrado, H. Mizutani, and A.H. Hoveyda J. Am. Chem. Soc. 124 2002 13362
38. R.R. Cesati III., J. De Armas, and A.H. Hoveyda J. Am. Chem. Soc. 126 2004 96
39. A.W. Hird, and A.H. Hoveyda Angew. Chem., Int. Ed. 42 2003 1276
40. D.M. Mampreian, and A.H. Hoveyda Org. Lett. 6 2004 2829
41. J. Wu, D.M. Mampreian, and A.H. Hoveyda J. Am. Chem. Soc. 127 2005 4584
42. M.A. Kacprzynski, S.A. Kazane, T.L. May, and A.H. Hoveyda Org. Lett. 9 2007 3187
43. F. Valleix, K. Nagai, T. Soeta, M. Kuriyama, K. Yamada, and K. Tomioka Tetrahedron 61 2005 7420
44. T. Soeta, M. Kuriyama, and K. Tomioka J. Org. Chem. 70 2005 297
45. T. Soeta, K. Selim, M. Kuriyama, and K. Tomioka Adv. Synth. Catal. 349 2007 629
46. T. Soeta, K. Selim, M. Kuriyama, and K. Tomioka Tetrahedron 63 2007 6573
47. F. Guillen, C.L. Winn, and A. Alexakis Tetrahedron: Asymmetry 12 2001 2083
48. J. Pytkowicz, S. Roland, and P. Mangeney Tetrahedron: Asymmetry 12 2001 2087
49. A. Alexakis, C.L. Winn, F. Guilen, J. Pytowitz, S. Roland, and P. Mangeney Adv. Synth. Catal. 345 2003 345
50. A.W. Hird, and A.H. Hoveyda J. Am. Chem. Soc. 127 2005 14988
51. M. Schinnerl, M. Seitz, A. Kaiser, and O. Reiser Org. Lett. 3 2001 4259
52. M.T. Barros, C.D. Maycock, and A.M.F. Phillips Tetrahedron: Asymmetry 16 2005 2946
53. Other examples of use of N,P-ligands: X. Hu, H. Chen, and X. Zhang Angew. Chem., Int. Ed. 38 1999 3518
54. T. Morimoto, Y. Yamaguchi, M. Suzuki, and A. Saitoh Tetrahedron Lett. 41 2000 10025
55. T. Morimoto, N. Obara, I. Yoshida, K. Tanaka, and T. Kan Tetrahedron Lett. 48 2007 3093
56. M. Hatano, T. Asai, and K. Ishihara Tetrahedron Lett. 48 2007 8590
57. Other examples of asymmetric 1,4-addition. G.Y. Ishmuratov, M.P. Yakovleva, V.A. Ganieva, G.R. Gareeva, R.R. Muslukhov, and G.A. Tolstikov Chem. Nat. Compd. 41 2005 549
58. R.K. Dieter, and M. Tokles J. Am. Chem. Soc. 109 1987 2040
59. M. Hayashi, Y. Miyamoto, T. Inoue, and N. Oguni J. Chem. Soc., Chem. Commun. 1991 1752
60. M. Hayashi, Y. Miyamoto, T. Inoue, and N. Oguni J. Org. Chem. 58 1993 1515
61. M. Hayashi, T. Inoue, and N. Oguni J. Chem. Soc., Chem. Commun. 1994 341
62. M. Hayashi, T. Inoue, Y. Miyamoto, and N. Oguni Tetrahedron 50 1994 4385
63. M. Hayashi, K. Yoshimoto, N. Hirata, K. Tanaka, N. Oguni, K. Harada, A. Matsushita, Y. Kawachi, and H. Sasaki Isr. J. Chem. 41 2001 241
64. T. Tanaka, Y. Yasuda, and M. Hayashi J. Org. Chem. 71 2006 7091
65. T. Tanaka, Y. Sano, and M. Hayashi Chem. Asian J. 3 2008 1465
66. T. Tanaka, and M. Hayashi Chem. Lett. 37 2008 1298
67. K. Kawamura, H. Fukuzawa, and M. Hayashi Org. Lett. 10 2008 3509
68. K. Kawamura, H. Fukuzawa, and M. Hayashi Bull. Chem. Soc. Jpn. 84 2011 640
69. D. Gerald, H. Bettina, and H. Gerald Tetrahedron: Asymmetry 10 1990 3297
70. K. Nienkemper, G. Kehr, and S. Kehr J. Organomet. Chem. 698 2008 1572
71. A.H.M. de Vries, R. Imbos, and B.L. Feringa Tetrahedron: Asymmetry 8 1997 1467
72. K. Endo, M. Ogawa, and T. Shibata Angew. Chem., Int. Ed. 49 2010 2410
73. T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki, and M. Kumada J. Org. Chem. 48 1983 2195