Enantioselective synthesis of optically pure β-amino ketones and γ-aryl amines by Rh-catalyzed asymmetric hydrogenation

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 332-334

  Geng, Huiling ^a,b   Huang, Kexuan ^b   Sun, Tian ^b   Li, Wei ^b   Zhang, Xiaowei ^b   Zhou, Le ^a   Wu, Wenjun ^a   Zhang, Xumu ^b  

^a NORTHWEST A F UNIVERSITY   (China)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINES; ASYMMETRIC HYDROGENATION; BIOACTIVE MOLECULES; BUILDING BLOCKES; ENAMIDES; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY;

AMINES; CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; KETONES; RHODIUM;

AMINATION;

AMIDE; AMINE; HYDROGEN; KETONE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; ONE POT SYNTHESIS; OPTICAL ROTATION; REACTION ANALYSIS; REDUCTION;

AMINES; CATALYSIS; HYDROGENATION; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 78650865159     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102091f     Document Type: Article

References (60)

1. Houben, J. H.; Weyl, T. In Houben-Weyl Methoden der Organischen Chemie, 4 th ed.; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, New York, 1977.
2. Kleinnmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed; Pergamon: New York, 1991.
3. Arend, M.; Wastermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044
4. Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791 For selected applications of β-amino ketones in the synthesis of natural products and biologically active compounds, see: Guo, D.-L.; Zhu, X.-W. Chem. Ind. Eng. 2008, 25, 276
5. Sham, H. L.; Kempf, D. J.; Molla, A. Antimicrob. Agents Chemother. 1998, 42, 3218
6. Hou, F.; Zhang, X.; Zhang, G.; Xie, D.; Chen, P.; Zhang, W.; Jiang, J.; Liang, M.; Liu, Z.; Geng, R. N. Engl. J. Med. 2006, 354, 131
7. Mukaiyama, T. Organic Reactions; Wiley: New York, 1982.
8. Wanner, K. T.; Horner, G. Tetrahedron 1991, 47, 1895
9. Tramontini, M. Synthesis 1982, 605
10. Brienne, M. J.; Ouannes, C.; Jacques, J. J. Bull. Soc. Chim. Fr. 1969, 106, 2395
11. Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131
12. Bartoli, G.; Cimarel, C.; Palmieri, G. J. Chem. Soc., Perkin Trans. 1 1994, 537
13. For the chiral auxiliary-based strategy, see: Denmark, S. E.; Weber, T.; Piotrowski, D. W. J. Am. Chem. Soc. 1987, 109, 2224
14. Colyer, J. T.; Andersen, N. G.; Tedrow, J. S.; Soukup, T. S.; Faul, M. M. J. Org. Chem. 2006, 71, 6859 For enzyme-assisted resolution, see: Conzalez-Sabin, J.; Gotor, W.; Rebolledo, F. Tetrahedron: Asymmetry 2002, 13, 1315
15. Nechab, M.; Azzi, N.; Vanthuyne, N.; Bertrand, M.; Gastaldi, S.; Gil, G. J. Org. Chem. 2007, 72, 6918
16. Couty, F.; David, O.; Durrat, F.; Evano, G.; Lakhdar, S.; Marrot, J.; Vargas-Sanchez, M. Eur. J. Org. Chem. 2006, 3479
17. Barluenga, J.; Tomás, M.; Kouznetsov, V.; Jardón, J.; Rubio, E. Synlett 1991, 821
18. Shustov, G. V.; Denisenko, S. N.; Chervin, I. I.; Asfandiarov, N. L.; Kostyanovsky, R. G. Tetrahedron 1985, 41, 5719
19. Clifton, J. E.; Collins, I.; Hallett, P.; Hartley, D.; Lunts, L. H. C.; Wicks, P. D. J. Med. Chem. 1982, 25, 670
20. Hou, F.; Zhang, X.; Zhang, G.; Xie, D.; Chen, P.; Zhang, W.; Jiang, J.; Liang, M.; Wang, G.; Liu, Zh.; Geng, R. New Engl. J. Med. 2006, 354, 131
21. Kondo, S.; Shibahara, S.; Takahashi, S.; Maeda, K.; Umezawa, H.; Ohno, M. J. Am. Chem. Soc. 1971, 93, 6305
22. Raju, B.; Mortell, K.; Anandan, S.; O'Dowd, H.; Gao, H.; Gomez, M.; Hackbarth, C.; Wu, C.; Wang, W.; Yuan, Z.; White, R.; Trias, J.; Patel, D. V. Bioorg. Med. Chem. Lett. 2003, 13, 2413
23. Sham, H. L.; Kempf, D J.; Molla, A. Antimicrob. Agents Chemother. 1998, 42, 3218
24. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: New York, 1992.
25. Rao, I. N.; Prabhakaran, E. N.; Das, S. K.; Iqbal, J. J. Org. Chem. 2003, 68, 4079
26. Gomtsyan, A.; Keoenig, R. J.; Lee, C. J. Org. Chem. 2001, 66, 3613
27. Dakin, H. D.; West, R. J. Biol. Chem. 1928, 78, 745
28. Buchanan, G. L. Chem. Soc. Rev. 1988, 17, 91
29. Xu, L.; Xia, C.; Li, L. J. Org. Chem. 2004, 69, 8482
30. For reviews, see: Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991
31. Jauristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983 For the preparation of β-amino ketones, see: Gaunt, M. J.; Spencer, J. B. Org. Lett. 2001, 3, 25
32. Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891
33. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109
34. For a comprehensive review, see: Tramontini, M. Synthesis 1973, 703 For the preparation of β-amino ketones, see: Blike, F. E. Org. React. 1942, 1, 303
35. Muraoka, T.; Kamiya, S.; Matsuda, S. I.; Itoh, K. Chem. Commun. 2003, 449
36. Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338
37. Ambhaikar, N. B.; Snyder, J. P.; Liotta, D. C. J. Am. Chem. Soc. 2003, 125, 3690
38. Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011
39. Davis, F. A.; Prasd, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925
40. Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918
41. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis I-III; Springer: Berlin, 1999.
42. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
43. Ojima, I. Catalytic Asymmetric Synthesis, 2 nd ed.; Wiley-VCH: New York, 2000.
44. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029
45. For the preparation of 1,3-diketones, see: Han, X.; Widenhoefer, R. A. J. Org. Chem. 2004, 69, 1738
46. Chen, J.; Zhang, W.; Geng, H.; Li, W.; Hou, G.; Lei, A.; Zhang, X. Angew. Chem., Int. Ed. 2009, 48, 800
47. For selective ligands in AH, see: Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646
48. Burk, M. J. Acc. Chem. Res. 2000, 33, 363
49. Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425
50. Tang, W.; Wang, W.; Chi, Y.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 3509
51. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223
52. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932
53. Rylander, P. N. Catalytic Hydrogenation in Organic Synthesis; Academic Press: New York, 1979.
54. Hartung, W. H.; Simonff, R. Org. React. 1953, 7, 263
55. Breitner, E.; Roginski, E.; Rylander, P. N. J. Org. Chem. 1959, 24, 1855
56. Mori, A.; Mizusaki, T.; Miyakawa, Y.; Ohashi, E.; Haga, T.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Tetrahedron 2006, 62, 11925
57. Sajiki, H; Hattori, K.; Hirota, K. J. Org. Chem. 1998, 63, 7990
58. Sajiki, H.; Hattori, K.; Hirota, K. J. Chem. Soc., Perkin Trans. 1 1998, 4043
59. Sugiura, M.; Kumahara, M.; Nakajima, M. Chem. Commun. 2009, 3585
60. Luo, H.-T; Kang, Y.-R.; Nie, H.-Y.; Chen, W.-Y.; Yang, L.-M. Fenzi Cuihua 2009, 23, 392