Copper-Catalyzed enantioselective hydrosilylation of ketones by using monodentate binaphthophosphepine ligands

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 68-73

  Junge, Kathrin ^a   Wendt, Bianca ^a   Addis, Daniele ^a   Zhou, Shaolin ^a   Das, Shoubhik ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Copper; Homogeneous catalysis; Hydrosilylation; Ketones; P ligands

Indexed keywords

ALIPHATIC KETONES; CARBONYL COMPOUNDS; CHEMICAL EQUATIONS; ENANTIOSELECTIVE; HIGH YIELD; HOMOGENEOUS CATALYSIS; MONODENTATES; P LIGANDS; REACTION PARAMETERS;

CARBONYLATION; CATALYSIS; CHEMICAL COMPOUNDS; COPPER; ENANTIOSELECTIVITY; HYDROSILYLATION; KETONES; LIGANDS; REACTION KINETICS;

CHELATION;

EID: 73949108650     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902442     Document Type: Article

References (95)

1. a) T. Ohkuma, R. Noyori in Transition Metals for Organic Synthesis, Vol.2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 29-121;
2. b) S. Gladiali, E. Alberico in Transition Metals for Organic Synthesis, Vol.2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 145-162;
3. c) H. Nishiyama in Transition Metals for Organic Synthesis, Vol.2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 182-189.
4. a) I. Ojima, M. Nihonyanagi, Y. Nagai, J. Chem. Soc. Chem. Commun. 1972, 938a;
5. b) I. Ojima, T. Kogure, M. Nihonyanagi, Y. Nagai, Bull. Chem. Soc. Jpn. 1972, 45, 3506;
6. c) I. Ojima, M. Nihonyanagi, Y. Nagai, Bull. Chem. Soc. Jpn. 1972, 45, 3722;
7. d) R. J. P. Corriu, J. J. E. Moreau, J. Chem. Soc. Chem. Commun. 1978, 38-39.
8. a) H. Nishiyama, K. Itoh in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, pp. 111-144;
9. b) Com-prehensive Handbook on Hydrosilylation (Ed.: B. Marciniec), Pergamon Press, Oxford, 1992;
10. c) Hydrosilylation: A Comprehensive Review on Recent Advances (Ed.: B. Marciniec), Springer, Heidelberg, 2009.
11. H. Brunner, W. Mehling, J. Organomet. Chem. 1984, 275, C17-C21.
12. a) W. S. Mahoney, D. M. Brestensky, J. M. Stryker, J. Am. Chem. Soc. 1988, 110, 291-293;
13. b) W. S. Mahoney, J. M. Stryker, J. Am. Chem. Soc. 1989, 111, 8818-8823;
14. c) D. M. Brestensky, J. M. Stryker, Tetrahedron Lett. 1989, 30, 5677-5680;
15. d) T. M. König, J. E Daeuble, D. M. Brestensky, J. M. Stryker, Tetrahedron Lett. 1990, 31, 3237-3240.
16. a) B. H. Lipshutz, J. Keith, P. Papa, R. Vivian, Tetrahedron Lett. 1998, 39, 4627-4630;
17. b) B. H. Lipshutz, W. Chrisman, K. Noson, P. Papa, J. A. Sclafani, R. W. Vivian, J. M. Keith, Tetrahedron 2000, 56, 2779-2788;
18. c) B. H. Lipshutz, W. Chrisman, K. Noson, J. Organomet. Chem. 2001, 624, 367-371.
19. a) D. H. Appella, Y. Moritani, R. Shintani, E. M- Ferreira, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9473-9474;
20. b) Y. Moritani, D. H. Appella, V. Jurkauskas, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 6797-6798;
21. c) J. Yun, S. L. Buchwald, Org. Lett. 2001, 3, 1129-1131;
22. d) V. Jurkauskas, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 2892-2893;
23. e) G. Hughes, M. Kimura, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11253-11258.
24. a) B. H. Lipshutz, K. Noson, W. Chrisman, J. Am. Chem. Soc. 2001, 123, 12917-12918;
25. b) B. H. Lipshutz, A. Lower, K. Noson, Org. Lett. 2002, 4, 4045-4048;
26. c) B. H. Lipshutz, K. Noson, W. Chrisman, A. Lower, J. Am. Chem. Soc. 2003, 125, 8779-8789;
27. d) B. H. Lipshutz, C. C. Caires, P. Kuipers, W. Chrisman, Org. Lett. 2003, 5, 3085-3088;
28. e) B. H. Lipshutz, N Tanaka, B. R. Taft, C.-T. Lee, Org. Lett. 2006, 8,1963-1966;
29. f) B. H. Lipshutz, A. Lower, R. J. Kucejko, K. Noson, Org. Lett. 2006, 8, 2969-2972;
30. g) B. H. Lipshutz, C.-T. Lee, F. M. Servesko, Org. Lett. 2007, 9, 4713-4716;
31. h) C.-T. Lee, B. H. Lipshutz, Org. Lett. 2008, 10, 4187-4190.
32. a) J. T. Issenhuth, S. Dagorne, S. Bellemin-Laponnaz, Adv. Synth. Catal. 2006, 348, 1991-1994;
33. b) S. Rendler, M. Oestreich, Angew. Chem. 2007, 119, 504-510;
34. Angew. Chem Int. Ed. 2007, 46, 498-504;
35. c) J. K. Kassube, H. Wadepohl, L. H. Gade, Adv. Synth. Catal. 2009, 351, 607-616.
36. a) S. Sirol, J. Courmarcel, N. Mostefai, O. Riant, Org. Lett. 2001, 3, 4111-4113;
37. b) J. Courmarcel, N Mostefai, S. Sirol, S. Choppin, O. Riant, Isr. J. Chem. 2001, 41, 231-240;
38. c) O. Riant, N. Mostefai, J. Courmarcel, Synthesis 2004, 2943-2958;
39. d) N. Mostefai, S. Sirol, J. Courmarcel, O. Riant, Synthesis 2007, 1265-1271.
40. D.-W. Lee, J. Yun, Tetrahedron Lett. 2004, 45, 5415-5417.
41. a) J. Wu, J.-X. Ji, A. S. Chan, Proc. Natl. Acad. Sci. USA 2005, 102, 3570-3575;
42. b) X.-C. Zhang, Y. Wu, F Yu, F-F Wu, J. Wu, A. S. Chan, Chem. Eur. J. 2009, 75, 5888-5891.
43. B. H. Lipshutz, B. A. Frieman, A. E. Tomaso, Jr., Angew. Chem. 2006, 118, 1281-1286;
44. Angew. Chem. Int. Ed. 2006, 45, 1259-1264.
45. a) M. L. Kantam, S. Laha, J. Yadav, P. R. Likhar, B. Sreedhar, B. M. Choudary, Adv. Synth. Catal. 2007, 349, 1797-1802;
46. b) M. L. Kantam, J. Yadav, S. Laha, P. Srinivas, B. Sreedhar, F Figueras, J. Org. Chem. 2009, 74, 4608-4611.
47. M. L. Kantam, S. Laha, J. Yadav, P. R. Likhar, B. Sreedhar, S. Jha, S. Bhargava, M. Udayakiran, B. Jagadeesh, Org. Lett. 2008, 10, 2979-2982.
48. a) E. Vedejs, O. Daugulis, S. T. Diver, J. Org. Chem. 1996, 61, 430-431;
49. b) G. Zanoni, S. Gladiali, A. Marchetti, P. Piccinini, I. Tredici, G. Vidari, Angew. Chem. 2004, 116, 864-867;
50. Angew. Chem. Int. Ed. 2004, 43, 846-849;
51. c) L. Charruault, V. Michelet, R. Taras, S. Gladiali, J.-P. Genet, Chem. Commun. 2004, 850-851;
52. d) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127,12234-12235;
53. e) J. E. Wilson, G. C. Fu, Angew. Chem. 2006, 118, 1454-1457;
54. Angew. Chem. Int. Ed. 2006, 45, 1426-1429;
55. f) Y. K. Chung, G. C. Fu, Angew. Chem. 2009, 121, 2259-2261;
56. Angew. Chem. Int. Ed. 2009, 48, 2225-2227;
57. g) N. Pinto, N. Fleury-Bregeot, A. Marinetti, Eur. J. Org. Chem. 2009, 146-151;
58. h) E. Alberico, I. Nieddu, R. Taras, S. Gladiali, Helv. Chim. Acta 2006, 89,1716-1729.
59. a) Y. Chi, X. Zhang, Tetrahedron Lett. 2002, 43, 4849-4852;
60. b) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U Dingerdissen, M. Beller, Tetrahedron Lett. 2002, 43, 4977-4980;
61. c) K. Junge, G. Oehme, A. Monsees, T. Riermeier, M. Beller, J. Organomet. Chem. 2003, 675, 91-96;
62. d) K. Junge, B. Hagemann, S. Enthaler, A. Spannenberg, M. Michalik, G. Oehme, M. Beller, Tetrahedron: Asymmetry 2004, 15, 2621-2631;
63. e) K. Junge, B. Hagemann, S. Enthaler, G. Oehme, A. Monsees, T. Riermeier, M. Beller, Angew. Chem. 2004, 116, 5176-5179;
64. Angew. Chem. Int. Ed. 2004, 43, 5066-5069;
65. f) B. Hagemann, K. Junge, S. Enthaler, M. Michalik, T. Riermeier, A. Monsees, M. Beller, Adv. Synth. Catal. 2005, 347, 1978-1986;
66. g) S. Enthaler, B. Hagemann, K. Junge, G. Erre, M. Beller, Eur. J. Org. Chem. 2006, 2912-2917;
67. h) S. Enthaler, G. Erre, K. Junge, J. Holz, A. Börner, E. Alberico, I. Nieddu, S. Gladiali, M. Beller, Org. Process Res. Dev. 2007, 11, 568-577;
68. i) S. Enthaler, G. Erre, K. Junge, D. Michalik, A. Spannenberg, F. Marras, S. Gladiali, M. Beller, Tetrahedron: Asymmetry 2007, 18, 1288-1298.
69. a) E. Alberico, I. Nieddu, R. Taras, S. Gladiali, Helv. Chim. Acta 2006, 89, 1716-1729;
70. b) S. Enthaler, B. Hagemann, S. Bhor, G. Anilkumar, M. K. Tse, B. Bitterlich, K. Junge, G. Erre, M. Beller, Adv. Synth. Catal. 2007, 349, 853-860.
71. a) S. Gladiali, A. Dore, D. Fabbri, O. De Lucchi, M. Manassero, Tetrahedron: Asymmetry 1994, 5, 511-514;
72. b) S. Gladiali, D. Fabbri, Chem. Ber./Recueil 1997, 130, 543-554;
73. c) G. Erre, S. Enthaler, K. Junge, S. Gladiali, M. Beller, J. Mol. Catal A 2008, 280, 148-155.
74. a) F. Lagasse, H. B. Kagan, Chem. Pharm. Bull. 2000, 48, 315- 324;
75. b) I. V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240;
76. Angew. Chem. Int. Ed. 2001, 40, 1197-1200.
77. a) I. Ojima, T. Kogure, Y. Nagai, Chem. Lett. 1973, 33, 541-544;
78. b) I. Ojima, T. Kogure, Y. Nagai, Tetrahedron Lett. 1974, 15, 1889-1892;
79. c) Y. Uozumi, T. Hayashi, J. Am. Chem Soc. 1991,113, 9887-9898;
80. d) Y. Uozumi, S.-Y. Lee, Y. Hayashi, Tetrahedron Lett. 1992, 33, 7185-7188;
81. e) T. Hayashi, Tetrahedron: Asymmetry 1993, 4, 2419-2422;
82. f) K. Kitayama, Y. Uozumi, T. Hayashi, J. Chem. Soc. Chem. Commun. 1995, 1533-1534;
83. g) T. Hayashi, S. Hirate, K. Kitayama, H. Tsuji, A. Torii, Y. Uozumi, J. Org. Chem. 2001, 66, 1441-1449;
84. h) J. F. Jensen, B. Y. Svendsen, T. V. la Cour, H. L. Pedersen, M. Johannsen, J. Am. Chem. Soc. 2002, 124, 4558-4559;
85. i) X.-X. Guo, J.-H. Xie, G.-H. Hou, W.-J. Shi, L.-X. Wang, Q.-L. Zhou, Tetrahedron: Asymmetry 2004, 15, 2231-2234;
86. j) X. Li, J. Song, D. Xu, L. Kong, Synthesis 2008, 925-931.
87. a) R. D. Kroshefsky, R. Webs, J. G. Yerkade, Inorg. Chem. 1979, 18, 469-472;
88. b) D. W. Allen, B. F. Taylor, J. Chem. Soc. Dalton Trans. 1982, 51-54;
89. c) D. E. Schiff, J. W. Richardson, Jr., R. A. Jacobson, A. H. Cowley, J. Lasch, J. G. Verkade, Inorg. Chem. 1984, 23, 3373-3377;
90. d) A. Suárez, M. A. Méndez-Rojas, A. Pizzano, Organometallics 2002, 21, 4611-4621;
91. e) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N Champion, P. Dellis, Angew. Chem. 2004, 116, 324-329;
92. Angew. Chem. Int. Ed. 2004, 43, 320-325;
93. f) S. Otto, A. Ionescu, A. Roodt, J. Organomet. Chem. 2005, 690, 4337-4342;
94. g) T. Kimura, T. Murai, Chem. Lett. 2004, 33, 878-879;
95. h) J. Holz, O. Zayas, H. Jiao, W. Baumann, A. Spannenberg, A. Monsees, T. H. Riermeier, J. Almena, R. Kadyrov, A. Borner, Chem. Eur. J. 2006, 12, 5001-5013.