Highly enantio-and diastereoselective synthesis of Iγ-amino alcohols from α,β-unsaturated imines through a one-pot β-boration/ reduction/oxidation sequence

Advanced Synthesis and Catalysis

Volumn 353, Issue 2-3, 2011, Pages 376-384

  Solé, Cristina ^a   Whiting, Andrew ^b   Gulyás, Henrik ^a   Fernández, Elena ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

copper; diastereoselective reduction oxidation; enantioselective boration; I amino alcohols

Indexed keywords

EID: 79951842451     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000842     Document Type: Article

References (68)

1. H.-U. Blaser, Chem. Rev. 1992, 92, 935
2. K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833
3. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 83.
4. S. Shibahara, S. Kondo, K. Maeda, H. Umezawa, M. Ohno, J. Am. Chem. Soc. 1972, 94, 4353
5. Y.-F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 1982, 104, 6456
6. S. Hashiguchi, A. Kawada, H. Natsugari, J. Chem. Soc. Perkin Trans. 1 1991, 2435
7. A. P. Kozikowski, Y.-Y. Chen, J. Org. Chem. 1981, 46, 5248
8. S. Knapp, Chem. Rev. 1995, 95, 1859.
9. B. M. Trost, V. Yeh, Angew. Chem. 2002, 114, 889
10. Angew. Chem. Int. Ed. 2002, 41, 861
11. Y. Ukaji, K. Yamamoto, T. Fukui, T. Fujisawa, Tetrahedron Lett. 1991, 32, 2919
12. S. E. Denmark, C. T. Chen, J. Am. Chem. Soc. 1992, 114, 10674
13. T. Fujisawa, R. Hayakawa, M. Shimizu, Tetrahedron Lett. 1992, 33, 7903
14. Y.-W. Zhong, P. Tian, G. Q. Lin, Tetrahedron: Asymmetry 2004, 126, 12236
15. S. Ishikawa, T. Hamda, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236
16. M. P. Krzeminski, A. Wojtczk, Tetrahedron Lett. 2005, 46, 8299.
17. W. Oppolzer, R. N. Radinow, Tetrahedron Lett. 1988, 29, 5645
18. B. T. Cho, N. Kim, Synth. Commun. 1995, 25, 167
19. J. Eilers, J. Wilken, J. Martens, Tetrahedron: Asymmetry 1996, 7, 2343
20. Th. Jennequin, S. Labat, L. Toupet, J.-C. Caille, M. Mauduit, Synlett 2008, 1669
21. Sh. Tang, J. He, Y. Sun, L. He, X. She, J. Org. Chem. 2010, 75, 1961
22. M. C. Turcu, P. Perkioe, L. T. Kanerva, Tetrahedron: Asymmetry 2010, 21, 739.
23. D. Liu, W. Gao, C. Wang, X. Zhang, Angew. Chem. 2005, 117, 1715
24. Angew. Chem. Int. Ed. 2005, 44, 1687
25. H. Geng, W. Zhang, J. Chen, G. Hou, L. Zhou, Y. Zou, W. Wu, X. Zhang, Angew. Chem. 2009, 121, 6168
26. Angew. Chem. Int. Ed. 2009, 48, 6052.
27. T. Kochi, T. P. Tang, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 6518
28. G. E. Keck, A. P. Truong, Org. Lett. 2002, 4, 3131
29. F. A. Davis, P. M. Gaspari, B. M. Nolt, P. Xu, J. Org. Chem. 2008, 73, 9619.
30. For early references on catalytic β-boration of α,β- unsaturated carbonyl compounds see
31. Y. G. Lawson, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, Chem. Commun. 1997, 2051
32. K. Takahashi, T. Isiyama, N. Miyaura, Chem. Lett. 2000, 982
33. H. Ito, H. Yamanaka, J. Tateiwa, A. Hosomi, Tetrahedron Lett. 2000, 41, 682
34. K. Takahashi, T. Isiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47
35. H. A. Ali, I. Goldberg, M. Srebnik, Organometallics 2001, 20, 3962
36. G. W. Kabalka, B. C. Das, S. Das, Tetrahedron Lett. 2002, 43, 2323.
37. F. J. A. Schiffner, K. Müther, M. Oestreich, Angew. Chem. 2010, 122, 1214
38. Angew. Chem. Int. Ed. 2010, 49, 1194.
39. J.-E Lee, J. Yun, Angew. Chem. 2008, 120, 151
40. Angew. Chem. Int. Ed. 2008, 47, 145
41. H.-S. Sim, X. Feng, J. Yun, Chem. Eur. J. 2009, 15, 1939
42. S. Mun, J.-E. Lee, J. Yun, Org. Lett. 2006, 8, 4887
43. H. Chea, H.-S. Sim, J. Yun, Adv. Synth. Catal. 2009, 351, 855
44. V. Lillo, A. Prieto, A. Bonet, M. M. Díaz Requejo, J. Ramírez, P. J. Pérez, E. Fernández, Organometallics 2009, 28, 659
45. W. J. Fleming, H. Müller-Bunz, V. Lillo, E. Fernández, P. J. Guiry, Org. Biomol. Chem. 2009, 7, 2520
46. I-H. Chen, L. Yin, W. Itano, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 11664
47. X. Feng, J. Yun, Chem. Commun. 2009, 6577
48. D. Hirsch-Weil, K. A. Abbound, S. Hong, Chem. Commun. 2010, 46, 7525
49. X. Feng, J. Yun, Chem. Eur. J. 2010, 16, 13609.
50. V. Lillo, M. J. Geier, S. A. Westcott, E. Fernández, Org. Biomol. Chem. 2009, 7, 4674.
51. A. Bonet, H. Gulyás, I. O. Koshevoy, F. Estevan, M. Sanaß, M. A. ßbeda, E. Fernández, Chem. Eur. J. 2010, 16, 6382.
52. T. Shiomi, T. Adachi, K. Toribatake, L. Zhou, H. Nishiyama, Chem. Commun. 2009, 5987.
53. A. Bonet, H. Gulyás, E. Fernández, Angew. Chem. 2010, 122, 5256
54. Angew. Chem. Int. Ed. 2010, 49, 5130.
55. C. Solé, E. Fernández, Chem. Asian J., 2009, 4, 1790.
56. R. J. Mears, H. E. Sailes, J. P. Watts, A. Whiting, J. Chem. Soc. Perkin. Trans. 1, 2000, 3250
57. H. E. Sailes, J. P. Watts, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2000, 3362.
58. A. Whiting, Tetrahedron Lett. 1991, 32, 1503
59. R. J. Mears, A. Whiting, Tetrahedron 1993, 49, 177
60. G. Conole, H. DeaSilva, R. J. Mears, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 1825.
61. H. Nöth, B. Wrackmeyer, Nuclear Magnetic Spectroscopy of Boron Compounds, Springer-Verlag, Berlin, 1978, pa 14.
62. V. K. Singh, Synthesis 1992, 605
63. G. Borg, D. A. Cogan, J. A. Ullman, Tetrahedron Lett. 1999, 40, 6709
64. S. Sengupta, D. Das, S. Mondal, Synlett 2001, 1464
65. J. Vabeno, M. Brisander, T. Lejon, K. Luthman, J. Org. Chem. 2002, 67, 9186.
66. J. T. Colyer, N. G. Andersen, J. S. Tedrow, T. S. Soukup, M. J. Faul, Org. Chem. 2006, 71, 6859.
67. V. V. Kuznetsov, O. Y. Valiakhmetova, S. A. Bochkor, Chem. Heterocycl. Comp. 2009, 45, 1004.
68. A theoretical study has been particularly launched into the origin of the anti-stereoselectivity of the acyclic 2a imine with borohydride in methanol and the results will be published elsewhere.