Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: Enantioselective synthesis of optically active 1,2-diols

Angewandte Chemie - International Edition

Volumn 52, Issue 42, 2013, Pages 11011-11015

  Toribatake, Kenji ^a   Nishiyama, Hisao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

asymmetric catalysis; boron; diols; enantioselectivity; rhodium

Indexed keywords

ASYMMETRIC CATALYSIS; DIOLS; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; OPTICALLY ACTIVE; RHODIUM CATALYSTS; TERMINAL ALKENES;

BORON; HYDROCARBONS; RHODIUM;

ENANTIOSELECTIVITY;

EID: 84885466170     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305181     Document Type: Article

References (80)

1. A. B. Smith a III, S. S.-Y. Chen, F. C. Nelson, J. M. Reichert, B. A. Salvatore, J. Am. Chem. Soc. 1995, 117, 12013
2. P. J. Pye, K. Rossen, S. A. Weissman, A. Maliakal, R. A. Reamer, R. Ball, N. N. Tsou, R. P. Volante, P. J. Reider, Chem. Eur. J. 2002, 8, 1372
3. S. H. Kang, J. W. Jeong, Y. S. Hwang, S. B. Lee, Angew. Chem. 2002, 114, 1450
4. Angew. Chem. Int. Ed. 2002, 41, 1392
5. P. Gupta, S. V. Naidu, P. Kumar, Tetrahedron Lett. 2004, 45, 849
6. B. J. Edagwa, C. M. Taylor, J. Org. Chem. 2009, 74, 4132
7. B. B. Lohray, A. S. Reddy, V. Bhushan, Tetrahedron: Asymmetry 1996, 7, 2411
8. L. M. Schultze, H. H. Chapman, N. J. P. Dubree, R. J. Jones, K. M. Kent, T. T. Lee, M. S. Louie, M. J. Postich, E. J. Prise, J. C. Rohloff, R. H. Yu, Tetrahedron Lett. 1998, 39, 1853.
9. H. C. Kolb, M. S. Vana Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483
10. M. C. Noe, M. A. Letavic, S. L. Show, Org. React. 2005, 66, 109-625
11. A. B. Zaitsev, H. Adolfsson, Synthesis 2006, 1725
12. S. Kobayashi, M. Sugiura, Adv. Synth. Catal. 2006, 348, 1496.
13. T. Ohkuma, N. Utsumi, M. Watanabe, K. Tsutsumi, N. Arai, K. Murata, Org. Lett. 2007, 9, 2565
14. R. Kadyrov, R. M. Koenigs, C. Brinkmann, D. Voigtlaender, M. Rueping, Angew. Chem. 2009, 121, 7693
15. Angew. Chem. Int. Ed. 2009, 48, 7556
16. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264
17. M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 1988, 110, 629
18. S. Jeulin, N. Champion, S. Duprata dea Paule, P. Dellis, V. Ratovelmanana-Vidal, J.-P. Genêt, Synthesis 2005, 3666. For transfer hydrogenation of α-hydroxyketones, see
19. D. J. Cross, J. A. Kenny, I. Houson, L. Campbell, T. Walsgrove, M. Wills, Tetrahedron: Asymmetry 2001, 12, 1801
20. D. S. Matharu, D. J. Morris, A. M. Kawamoto, G. J. Clarkson, M. Wills, Org. Lett. 2005, 7, 5489
21. T. Hamada, T. Torii, K. Izawa, T. Ikariya, Tetrahedron 2004, 60, 7411.
22. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936
23. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307.
24. N. Bala, S. S. Chimni, Tetrahedron: Asymmetry 2010, 21, 2879. Selected achievements of microbial reactions
25. Y. Nie, Y. Xu, X. Q. Mu, Org. Process Res. Dev. 2004, 8, 246
26. Z. Liu, J. Michel, Z. Wang, B. Witholt, Z. Li, Tetrahedron: Asymmetry 2006, 17, 47
27. S. Hwang, C. Y. Choi, E. Y. Lee, Biotechnol. Lett. 2008, 30, 1219
28. P. Mahajabeen, A. Chadha, Tetrahedron: Asymmetry 2011, 22, 2156.
29. C. J. R. Bataille, T. J. Donohoe, Chem. Soc. Rev. 2011, 40, 114.
30. K. Suzuki, P. D. Oldenburg, L. Que, Jr., Angew. Chem. 2008, 120, 1913
31. Angew. Chem. Int. Ed. 2008, 47, 1887
32. T. W.-S. Chow, E. L.-M. Wong, Z. Guo, Y. Liu, J.-S. Huang, C.-M. Che, J. Am. Chem. Soc. 2010, 132, 13229.
33. I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320
34. H. E. Burks, J. P. Morken, Chem. Commun. 2007, 4717.
35. R. T. Baker, P. Nguyen, T. B. Marder, S. A. Westcott, Angew. Chem. 1995, 107, 1451
36. Angew. Chem. Int. Ed. Engl. 1995, 34, 1336
37. C. Dai, E. G. Robins, A. J. Scott, W. Clegg, D. S. Yufit, J. A. K. Howard, T. B. Marder, Chem. Commun. 1998, 1983
38. P. Nugyen, R. B. Coapes, A. D. Woodward, N. J. Taylor, J. M. Burke, J. A. K. Howard, T. B. Marder, J. Organomet. Chem. 2002, 652, 77
39. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun. 1997, 689
40. C. N. Iverson, M. R. Smith a III, Organometallics 1997, 16, 2757
41. J. Ramírez, R. Corberán, M. Sanaú, E. Peris, E. Fernandez, Chem. Commun. 2005, 3056
42. R. Corberán, J. Ramírez, M. Poyatos, E. Peris, E. Fernández, Tetrahedron: Asymmetry 2006, 17, 1759
43. V. Lillo, M. R. Fructos, J. Ramírez, A. A. C. Braga, F. Maseras, M. M. Díaz-Requejo, P. J. Pérez, E. Fernández, Chem. Eur. J. 2007, 13, 2614. For a theoretical approach, see
44. L. Dang, H. Zhao, Z. Lin, T. B. Marder, Organometallics 2007, 26, 2824
45. L. Dang, H. Zhao, Z. Lin, T. B. Marder, Organometallics 2008, 27, 1178. For asymmetric induction, see
46. T. B. Marder, N. C. Norman, C. R. Rice, Tetrahedron Lett. 1998, 39, 155.
47. J. B. Morgan, S. P. Miller, J. P. Morken, J. Am. Chem. Soc. 2003, 125, 8702
48. S. Trudeau, J. B. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem. 2005, 70, 9538
49. S. P. Miller, J. B. Morgan, F. J. Nepveux, J. P. Morken, Org. Lett. 2004, 6, 131.
50. L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 13210; for dienes as substrates
51. N. F. Pelz, A. R. Woodward, H. E. Burks, J. D. Sieber, J. P. Morken, J. Am. Chem. Soc. 2004, 126, 16328
52. H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134
53. K. Hong, J. P. Morken, J. Org. Chem. 2011, 76, 9102
54. L. T. Kliman, S. N. Mlynarski, G. E. Ferris, J. P. Morken, Angew. Chem. 2012, 124, 536
55. Angew. Chem. Int. Ed. 2012, 51, 521
56. G. E. Ferris, K. Hong, I. A. Roundtree, J. P. Morken, J. Am. Chem. Soc. 2013, 135, 2501.
57. V. Lillo, A. Bonet, E. Fernández, Dalton Trans. 2009, 2899
58. L. Dang, Z. Lin, T. B. Marder, Chem. Commun. 2009, 3987
59. J. A. Schiffner, K. Müther, M. Oestreich, Angew. Chem. 2010, 122, 1214
60. Angew. Chem. Int. Ed. 2010, 49, 1194
61. E. Hartmann, D. J. Vyas, M. Oestreich, Chem. Commun. 2011, 47, 7917
62. A. D. J. Calow, A. Whiting, Org. Biomol. Chem. 2012, 10, 5485. For other reviews of catalytic boration
63. T. Ohmura, M. Suginome, Bull. Chem. Soc. Jpn. 2009, 82, 29
64. J. Takaya, N. Iwasawa, ACS Catal. 2012, 2, 1993.
65. K. Lee, A. R. Zhugralin, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 7253
66. A. Bonet, H. Gulyás, E. Fernández, Angew. Chem. 2010, 122, 5256
67. Angew. Chem. Int. Ed. 2010, 49, 5130
68. C. Pubill-Ulldemolins, A. Bonet, C. Bo, H. Gulyás, E. Fernández, Chem. Eur. J. 2012, 18, 1121
69. H. Wu, S. Radomkit, J. M. O'Brien, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 8277.
70. A. Bonet, C. Pubill-Ulldemolins, C. Bo, H. Gulyás, E. Fernández, Angew. Chem. 2011, 123, 7296
71. Angew. Chem. Int. Ed. 2011, 50, 7158
72. A. Bonet, C. Sole, H. Gulyás, E. Fernández, Org. Biomol. Chem. 2012, 10, 6621.
73. T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, H. Nishiyama, Chem. Commun. 2009, 5987
74. K. Toribatake, L. Zhou, A. Tsuruta, H. Nishiyama, Tetrahedron 2013, 69, 3551. For preparation of [Rh(Phebox)] catalysts, see
75. Y. Kanazawa, Y. Tsuchiya, K. Kobayashi, T. Shiomi, J. Itoh, M. Kikuchi, Y. Yamamoto, H. Nishiyama, Chem. Eur. J. 2006, 12, 63
76. J. Ito, T. Shiomi, H. Nishiyama, Adv. Synth. Catal. 2006, 348, 1235. For reviews on applications of [Rh(Phebox)] catalysts, see
77. H. Nishiyama, J. Ito, Chem. Commun. 2010, 46, 203
78. J. Ito, H. Nishiyama, Synlett 2012, 509.
79. C. Pubill-Ulldemolins, M. Poyatos, C. Bo, E. Fernández, Dalton Trans. 2013, 42, 746. Rh/NHC-catalyzed diboration and theoretical explanation.
80. T. Shimada, K. Mukaide, A. Shinohara, J. W. Han, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 1584.