Synthesis of a chiral N-heterocyclic carbene bearing a m-terphenyl-based phosphate moiety as an anionic N-substituent and its application to copper-catalyzed enantioselective boron conjugate additions

Tetrahedron Asymmetry

Volumn 24, Issue 12, 2013, Pages 729-735

  Iwai, Tomohiro ^a   Akiyama, Yuki ^a   Sawamura, Masaya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE; BORON; CARBENE; COPPER; HETEROCYCLIC COMPOUND; PHOSPHATE; RHODIUM COMPLEX; TERPHENYL DERIVATIVE;

ANION EXCHANGE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHIRALITY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION;

EID: 84879360232     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.05.013     Document Type: Article

References (59)

1. S. Díez-González N-Heterocyclic Carbenes 2011 RSC-Publishing Cambridge
2. O. Kühl Functionalised N-Heterocyclic Carbene Complexes 2010 Wiley-VCH Weinheim
3. S. Díez-González, N. Marion, and S.P. Nolan Chem. Rev. 109 2009 3612
4. N-Heterocyclic Carbenes in Transition Metal Catalysis F. Glorius Topics in Organometallic Chemistry 2007 Springer Berlin/Heidelberg Vol. 21
5. S.P. Nolan N-Heterocyclic Carbenes in Synthesis 2006 Wiley-VCH Weinheim
6. For reviews, see F. Wang, L.-J. Liu, W. Wang, S. Li, and M. Shi Coord. Chem. Rev. 256 2012 804
7. V. César, S. Bellemin-Laponnaz, and L.H. Gade Chem. Soc. Rev. 33 2004 619
8. M.C. Perry, and K. Burgess Tetrahedron: Asymmetry 14 2003 951
9. P.L. Arnold, A.C. Scarisbrick, A.J. Blake, and C. Wilson Chem. Commun. 2001 2340
10. J.J. Van Veldhuizen, S.B. Garber, J.S. Kingsbury, and A.H. Hoveyda J. Am. Chem. Soc. 124 2002 4954
11. J.J. Van Veldhuizen, D.G. Gillingham, S.B. Garber, O. Kataoka, and A.H. Hoveyda J. Am. Chem. Soc. 125 2003 12502
12. P.L. Arnold, M. Rodden, K.M. Davis, A.C. Scarisbrick, A.J. Blake, and C. Wilson Chem. Commun. 2004 1612
13. A.O. Larsen, W. Leu, C.N. Oberhuber, J.E. Campbell, and A.H. Hoveyda J. Am. Chem. Soc. 126 2004 11130
14. H. Clavier, L. Coutable, J.-C. Guillemin, and M. Mauduit Tetrahedron: Asymmetry 16 2005 921
15. J.J. Van Veldhuizen, J.E. Campbell, R.E. Giudici, and A.H. Hoveyda J. Am. Chem. Soc. 127 2005 6877
16. H. Clavier, L. Coutable, L. Toupet, J.-C. Guillemin, and M. Mauduit J. Organomet. Chem. 690 2005 5237
17. K.-S. Lee, M.K. Brown, A.W. Hird, and A.H. Hoveyda J. Am. Chem. Soc. 128 2006 7182
18. D. Martin, S. Kehrli, M. d'Augustin, H. Clavier, M. Mauduit, and A. Alexakis J. Am. Chem. Soc. 128 2006 8416
19. J. Wencel, M. Mauduit, H. Hénon, S. Kehrli, and A. Alexakis Aldrichim. Acta 42 2009 43
20. S. Kehrli, D. Martin, D. Rix, M. Mauduit, and A. Alexakis Chem. Eur. J. 16 2010 9890
21. M. Tissot, A.P. Hernández, D. Müller, M. Mauduit, and A. Alexakis Org. Lett. 13 2011 1524
22. R. Shintani, K. Takatsu, M. Takeda, and T. Hayashi Angew. Chem., Int. Ed. 50 2011 8656
23. M. Tissot, D. Poggiali, H. Hénon, D. Müller, L. Guénée, M. Mauduit, and A. Alexakis Chem. Eur. J. 18 2012 8731
24. N. Germain, M. Magrez, S. Kehrli, M. Mauduit, and A. Alexakis Eur. J. Org. Chem. 2012 5301
25. M.K. Brown, T.L. May, C.A. Baxter, and A.H. Hoveyda Angew. Chem., Int. Ed. 46 2007 1097
26. M.A. Kacprzynski, T.L. May, S.A. Kazane, and A.H. Hoveyda Angew. Chem., Int. Ed. 46 2007 4554
27. Y. Lee, K. Akiyama, D.G. Gillingham, M.K. Brown, and A.H. Hoveyda J. Am. Chem. Soc. 130 2008 446
28. T.L. May, M.K. Brown, and A.H. Hoveyda Angew. Chem., Int. Ed. 47 2008 7358
29. Y. Lee, B. Li, and A.H. Hoveyda J. Am. Chem. Soc. 131 2009 11625
30. K. Akiyama, F. Gao, and A.H. Hoveyda Angew. Chem., Int. Ed. 49 2010 419
31. B. Jung, and A.H. Hoveyda J. Am. Chem. Soc. 134 2012 1490
32. S. Sakaguchi, K.S. Yoo, J. O'Neill, J.H. Lee, T. Stewart, and K.W. Jung Angew. Chem., Int. Ed. 47 2008 9326
33. K.S. Yoo, J. O'Neill, S. Sakaguchi, R. Giles, J.H. Lee, and K.W. Jung J. Org. Chem. 75 2010 95
34. S. Sakaguchi, M. Kawakami, J. O'Neill, K.S. Yoo, and K.W. Jung J. Organomet. Chem. 695 2010 195
35. R. Kamisue, and S. Sakaguchi J. Organomet. Chem. 696 2011 1910
36. M. Yoshimura, N. Shibata, M. Kawakami, and S. Sakaguchi Tetrahedron 68 2012 3512
37. G.L. Hamilton, E.J. Kang, M. Mba, and F.D. Toste Science 317 2007 496
38. K. Ohmatsu, M. Ito, T. Kunieda, and T. Ooi Nat. Chem. 4 2012 473
39. T. Akiyama, J. Itoh, and K. Fuchibe Adv. Synth. Catal. 348 2006 999
40. T. Akiyama Chem. Rev. 107 2007 5744
41. M. Terada Bull. Chem. Soc. Jpn. 83 2010 101
42. P. Baret, C. Béguin, D. Gaude, G. Gellon, C. Mourral, J.-L. Pierre, G. Serratrice, and A. Favier Tetrahedron 50 1994 2077
43. J.A. Schiffner, K. Müther, and M. Oestreich Angew. Chem., Int. Ed. 49 2010 1194 For reviews, see
44. E. Hartmann, D.J. Vyas, and M. Oestreich Chem. Commun. 47 2011 7917
45. S. Mun, J.-E. Lee, and J. Yun Org. Lett. 8 2006 4887 For the enantioselective copper-catalyzed boron conjugate addition with phosphine- or amine-based chral ligands, see
46. D. Lee, D. Kim, and J. Yun Angew. Chem., Int. Ed. 45 2006 2785
47. J.-E. Lee, and J. Yun Angew. Chem., Int. Ed. 47 2008 145
48. W.J. Fleming, H. Müller-Bunz, V. Lillo, E. Fernández, and P.J. Guiry Org. Biomol. Chem. 7 2009 2520
49. X. Feng, and J. Yun Chem. Commun. 2009 6577
50. X. Feng, and J. Yun Chem. Eur. J. 16 2010 13609
51. C. Solé, A. Whiting, H. Gulyás, and E. Fernández Adv. Synth. Catal. 353 2011 376
52. J.C.H. Lee, R. McDonald, and D.G. Hall Nat. Chem. 3 2011 894
53. A.R. Burns, J.S. González, and H.W. Lam Angew. Chem., Int. Ed. 51 2012 10827
54. S. Kobayashi, P. Xu, T. Endo, M. Ueno, and T. Kitanosono Angew. Chem., Int. Ed. 51 2012 12763
55. V. Lillo, A. Prieto, A. Bonet, M.M. Díaz-Requejo, J. Ramírez, P.J. Pérez, and E. Fernández Organometallics 28 2009 659 For enantioselective copper-catalyzed boron conjugate additions with chiral NHC ligands, see
56. J.K. Park, H.H. Lackey, M.D. Rexford, K. Kovnir, M. Shatruk, and D.T. McQuade Org. Lett. 12 2010 5008
57. D. Hirsch-Weil, K.A. Abboud, and S. Hong Chem. Commun. 46 2010 7525
58. J.M. O'Brien, K.-S. Lee, and A.H. Hoveyda J. Am. Chem. Soc. 132 2010 10630
59. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953 Research