Enantiodivergent synthesis of P-chirogenic phosphines

Comptes Rendus Chimie

Volumn 13, Issue 8-9, 2010, Pages 1213-1226

  Chaux, Fanny ^a   Frynas, Slawomir ^a   Laureano, Hugo ^a,b   Salomon, Christine ^a   Morata, Gérald ^a   Auclair, Marie Laure ^a   Stephan, Michel ^c   Merds, Rachid ^c   Richard, Philippe ^a   Ondel Eymin, Marie Jo ^a   Henry, Jean Christophe ^b   Bayardon, Jérôme ^a   Darcel, Christophe ^a   Jugé, Sylvain ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b SYNTHELOR SAS   (France)

^c PSL RESEARCH UNIVERSITY   (France)

Author keywords

Asymmetric synthesis; Borane complexes; Chiral phosphines; Enantiomers

Indexed keywords

EID: 77956611977     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2010.06.001     Document Type: Article

References (75)

1. W. Tang, and X. Zang Chem. Rev 103 2003 3029
2. E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive asymmetric catalysis 2004 Springer N.Y
3. H. Shimidzu, I. Nagasaki, and T. Saito Tetrahedron 61 2005 5405
4. R.G. Arrayas, J. Adrio, and J.C. Carretero Angew. Chem. Int. Ed 45 2006 7674
5. G.C. Hargaden, and P.J. Guiry Chem. Rev 109 2009 2505
6. A. Borner, Phosphorous ligands in asymmetric catalysis vol.3 2008 Wiley-VCH Weinheim
7. H.B. Kagan, and M. Sasaki F.R. Hartley, The chemistry of organophosphorus compounds vol. 1 1990 J. Wiley
8. K. Pietrusiewicz, and M. Zablocka Chem. Rev 94 1994 1375
9. O.I. Kolodiazhnyi Tetrahedron: Asymmetry 9 1998 1279
10. M. Berthod, G. Mignani, G. Woodward, and M. Lemaire Chem. Rev 105 2005 1801
11. A. Grabulosa, J. Granell, and G. Muller Coord. Chem. Rev 251 2007 25
12. K.V.L. Crépy, and T. Imamoto Top. Curr. Chem 229 2003 1
13. T. Imamoto J. Synth. Org. Chem. Jpn 65 2007 1060
14. M. Ohff, J. Holz, M. Quirmbach, and A. Börner Synthesis 1998 1391
15. C. Darcel, J. Uziel, and S Jugé A. Borner, Phosphorous Ligands in Asymmetric Catalysis vol. 3 2008 Wiley-VCH Weinheim 1211
16. N. Andrushko, and A. Börner A. Borner, Phosphorous Ligands in Asymmetric Catalysis vol. 3 2008 Wiley-VCH Weinheim 1275
17. S. Jugé Phosphorus Sulfur Silicon Relat. Compd 183 2008 233
18. U. Nagel, and B. Rieger Organometallics 8 1989 1534
19. U. Nagel, C. Roller, and Z. Naturforsch B: Chem. Sci. 53 1998 267
20. D. Moulin, C. Darcel, and S. Jugé Tetrahedron: Asymmetry 10 1999 4729
21. C. Darcel, D. Moulin, J.C. Henry, M. Lagrelette, P. Richard, P. Harvey, and S. Jugé Eur. J. Org. Chem 13 2007 2078
22. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, and R. Noyori J. Org. Chem 51 1986 629
23. R. Schmidt, J. Foricher, M. Cereghetti, and P. Schönholzer Helv. Chim. Acta 74 1991 370
24. S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.P. Genêt, N. Champion, G. Deschaux, and P. Dellis Org. Process. Res. Dev 7 2003 399
25. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, and A. Tijani J. Am. Chem. Soc 116 1994 4062
26. M. van der Berg, A.J. Minnaard, R.M. Haak, M. Leeman, E.P. Schudde, A. Meetsma, B.L. Feringa, A.H.M. de Vries, C.E.P. Maljaars, C.E. Willans, D. Hyett, J.A.F. Boogers, H.J.W. Henderickx, and J.G. de Vries Adv. Synth. Catal 345 2003 308
27. H.B. Kagan, and T.P. Dang J. Am. Chem. Soc 94 1972 6429
28. G. Helmchen, and G. Pfaltz Acc. Chem. Res 33 2000 336
29. E. Bélanger, M.F. Pouliot, and J.F. Paquin Org. Lett 11 2009 2201
30. M.J. Burk, J.E. Feaster, W.A. Nugent, and R.L. Harlow J. Am. Chem. Soc 115 1993 10125
31. B.D. Vineyard, W.S. Knowles, M.J. Sabacky, G.L. Bachman, and D.J. Weinkauff J. Am. Chem. Soc 99 1977 5946
32. F. Mathey, F. Mercier, F. Robin, and L. Ricard J. Organomet. Chem 577 1998 117
33. G. Hoge, H.P. Wu, W.S. Kissel, D.A. Pflum, D.J. Greene, and J. Bao J. Am. Chem. Soc 126 2004 5966
34. A.R. Muci, K.R. Campos, and D.A. Evans J. Am. Chem. Soc 117 1995 9075
35. K. Nagata, S. Matsukawa, and T. Imamoto J. Org. Chem 65 2000 4185
36. B. Wolfe, and T. Livinghouse J. Am. Chem. Soc 120 1998 5116
37. H. Heath, B. Wolfe, T. Livinghouse, and S.K. Bae Synthesis 15 2001 2341
38. Y. Yamanoi, and T. Imamoto J. Am. Chem. Soc 64 1999 2988
39. A. Ohashi, S.I. Kikuchi, M. Yasutake, and T. Imamoto Eur. J. Org. Chem. 2002 2535
40. T. Imamoto, A. Kumada, and K. Yoshida Chem. Lett. 36 2007 500
41. G. Hoge J. Am. Chem. Soc 125 2003 10219
42. J.J. Gammon, P. OBrien, and B. Kelly Org. Lett. 11 2009 5022
43. J.J. Gammon, S.J. Canipa, P. OBrien, B. Kelly, and S. Taylor Chem. Commun. 2008 3750
44. S. Jugé, J.P. Genêt, Fr. Patent, Fr 2 603 286 (1986) and intern. extensions;
45. S. Jugé, M. Stéphan, J.A. Laffitte, and J.P. Genêt Tetrahedron Lett. 31 1990 6357
46. S. Jugé, M. Stéphan, R. Merds, J.P. Genêt, and S. Halut-Desportes J. Chem. Soc. Chem. Commun. 1993 531
47. E.B. Kaloun, R. Merds, J.P. Genêt, J. Uziel, and S. Jugé J. Organomet. Chem. 529 1997 455
48. S. Humbel, C. Bertrand, C. Darcel, C. Bauduin, and S. Jugé Inorg. Chem 42 2003 420
49. C. Bauduin, D. Moulin, E.B. Kaloun, C. Darcel, and S. Jugé J. Org. Chem. 68 2003 4293
50. D. Vinci, N. Mateus, X. Wu, F. Hancock, A. Steiner, and J. Xiao Org. Lett. 8 2006 215
51. S. Jugé, J.P. Genêt, J.A. Laffitte, M. Stéphan, French Patent 91 01674
52. R. Merds, PhD thesis Université Pierre & Marie Curie - Paris, France, 1993.
53. C. Darcel, E.B. Kaloun, R. Merds, D. Moulin, N. Riegel, S. Thorimbert, J.P. Genêt, and S. Jugé J. Organomet. Chem. 624 2001 333
54. J. Uziel, N. Riegel, B. Aka, P. Figuire, and S. Jugé Tetrahedron Lett 38 1997 3405
55. T. Imamoto, K. Hirose, H. Amano, and H. Seki Main. Group. Chem. 1 1996 331
56. J. Uziel, C. Darcel, D. Moulin, C. Bauduin, and S. Jugé Tetrahedron: Asymmetry 12 2001 1441
57. N. Brodie, and S. Jugé Inorg. Chem 37 1998 2438
58. T. Imamoto, T. Kusumoto, N. Suzuki, and K. Sato J. Am. Chem. Soc 107 1985 5301
59. H. Brisset, Y. Gourdel, P. Pellon, and M. Le Corre Tetrahedron Lett 34 1993 4523
60. H. Yang, N. Lugan, and R. Mathieu Organometallics 16 1997 2089
61. G. Knühl, P. Sennhenn, and G. Helmchen J. Chem. Soc. Chem. Commun 1995 1845
62. L. McKinstry, J.J. Overberg, C. Soubra-Ghaoui, D.S. Walsh, K.A. Robins, T.T. Toto, and J.L. Toto J. Org. Chem 65 2000 2261
63. D. Moulin, S. Bago, C. Bauduin, C. Darcel, and S. Jugé Tetrahedron: Asymmetry 11 2000 3939
64. M. Schröder, K. Nozaki, and T. Hiyama Bull. Chem. Soc. Jpn 77 2004 1931
65. A. Pelter, R. Rosser, and S. Mills J. Chem. Soc. Chem. Commun 1981 1014
66. K. Tani, L.D. Brown, J. Ahmed, J.A. Ibers, M. Yokota, A. Nakamura, and S. Otsuka J. Am. Chem. Soc 99 1977 7876
67. W.D. Ollis, M. Rey, and I.O. Sutherland J. Chem. Soc. Perkin Trans. I 1983 1009
68. V.V. Dunina, L.G. Kuzmina, M.Y. Kazakova, Y.K. Grishin, Y.A. Veits, and E.I. Kazakova Tetrahedron: Asymmetry 8 1997 2537
69. M. Deshmukh, E. Dunach, S. Jugé, and H.B. Kagan Tetrahedron Lett 25 1984 3467
70. E. Dunach, and H.B. Kagan Tetrahedron Lett. 25 1985 2649
71. F. Maienza, F. Spindler, M. Thommen, B. Pugin, C. Malan, and A. Mezzetti J. Org. Chem 67 2002 5239
72. E.A. Colbi, and T.F. Jamison J. Org. Chem 68 2003 156
73. A. Altomare, G. Cascarano, C. Giacovazzo, and A. Guagliardi J. Appl. Crystallogr 26 1993 343
74. G.M. Sheldrick SHELX97 (Includes SHELXS97 and SHELXL97), Release 97-2, Programs for Crystal Structure Analysis 1998 Institüt für Anorganische Chemie, University of Göttingen, Tammanstrasse 4 D-3400 Göttingen, Germany
75. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837