Axial [6,6′-(2,4-pentadioxy)]-1,1′-biphenyl-2,2′-diamine (PD-BIPHAM): practical synthesis and applications in asymmetric hydrogenation

Tetrahedron

Volumn 66, Issue 21, 2010, Pages 3702-3706

  Wang, Chun Jiang ^a,b   Xu, Zhong Ping ^a   Wang, Xiang ^c   Teng, Huai Long ^a  

^a WUHAN UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

^c WUHAN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Asymmetric hydrogenation; Axial biphenyl diamine; Axial chirality; Central chirality; PD BIPHAM

Indexed keywords

[6,6' ( 2,4 PENTADIOXY)] 1,1' BIPHENYL 2,2' DIAMINE; AMINO ACID DERIVATIVE; BIPHENYL DERIVATIVE; BIPHENYL DIAMINE; DIAMINE DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; ATOM; BIOTRANSFORMATION; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; HYDROGENATION; METHODOLOGY; PRIORITY JOURNAL;

EID: 77951113101     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.073     Document Type: Article

References (95)

1. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, Weinheim
2. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III (1999), Springer, Berlin
3. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Wiley, New York, NY
4. In: Andersson P.G., and Munslow I.J. (Eds). Modern Reduction Methods (2008), Wiley-VCH, Weinheim
5. For recent reviews, see:
6. Chen Y., Yekta S., and Yudin A.K. Chem. Rev. 103 (2003) 3155
7. Brunel J.M. Chem. Rev. 105 (2005) 857 and 2007, 107, PR1
8. Berthod M., Mignani G., Woodward G., and Lemaire M. Chem. Rev. 105 (2005) 1801
9. Telfer S.G., and Kuroda R. Coord. Chem. Rev. 242 (2003) 33
10. Ding K.-L., Guo H.C., Li X., Yuan Y., and Wang Y. Top. Catal. 35 (2005) 105
11. Rao R.K., Naidu A.B., Jaseer E.A., and Sekar G. Tetrahedron 65 (2009) 4619
12. Thakur K.G., Jaseer E.A., Naidu A.B., and Sekar G. Tetrahedron Lett. 50 (2009) 2865
13. Mannam S., and Sekar G. Tetrahedron: Asymmetry 20 (2009) 497
14. Alamsetti S.K., Mannam S., Mutupandi P., and Sekar G. Chem.-Eur. J. 15 (2009) 1086
15. Prasad D.J.C., Naidu A.B., and Sekar G. Tetrahedron Lett. 50 (2009) 1411
16. Naidu A.B., and Sekar G. Tetrahedron Lett. 49 (2008) 3147
17. Hatano M., Ikeno T., Matsumura T., Torii S., and Ishihara K. Adv. Synth. Catal. 350 (2008) 1776
18. Hannedouche J., Aillaud I., Collin J., Schulz E., and Trifonov A. Chem. Commun. (2008) 3552
19. Chianese A.R., and Crabtree R.H. Organometallics 24 (2005) 4432
20. Faller J.W., and Fontaine P.P. Organometallics 24 (2005) 4132
21. Chen X., Guo R., Li Y., Chen G., Yeung C.-H., and Chan A.S.C. Tetrahedron: Asymmetry 15 (2004) 213
22. Suga H., Kakehi A., and Mitsuda M. Chem. Lett. (2002) 900
23. Suga H., Kakehi A., and Mitsuda M. Bull. Chem. Soc. Jpn. 77 (2004) 561
24. Suga H., Kitamura T., Kakehi A., and Baba T. Chem. Commun. (2004) 1414
25. Suga H., Kakehi A., Ito S., and Sugimoto H. Bull. Chem. Soc. Jpn. 76 (2003) 327
26. Suga H., Nakajima T., Itoh K., and Kakehi A. Org. Lett. 7 (2005) 1431
27. Suga H., Funyu A., and Kakehi A. Org. Lett. 9 (2007) 97
28. Zhang T., Shi M., and Zhao M. Tetrahedron 64 (2008) 2412
29. Zhang T., Wang W., Gu X., and Shi M. Organometallics 27 (2008) 753
30. Liu Z., Zhang T., and Shi M. Organometallics 27 (2008) 2668
31. Guillena G., Najera C., and Viozquez S.F. Synlett (2008) 3031
32. Guillena G., Hita M.C., Najera C., and Viozquez S.F. J. Org. Chem. 73 (2008) 5933
33. Guillena G., Hita M.C., Najera C., and Viozquez S.F. Tetrahedron: Asymmetry 18 (2007) 2300
34. Guillena G., Hita M.C., and Najera C. Tetrahedron: Asymmetry 18 (2007) 1272
35. Guillena G., Hita M.C., and Najera C. Tetrahedron: Asymmetry 17 (2006) 1493
36. Guillena G., Hita M.C., and Najera C. Tetrahedron: Asymmetry 17 (2006) 1027
37. Guillena G., Hita M.C., and Najera C. Tetrahedron: Asymmetry 17 (2006) 729
38. Sakakura A., Suzuki K., Nakano K., and Ishihara K. Org. Lett. 8 (2006) 2229
39. Sakakura A., Suzuki K., and Ishihara K. Adv. Synth. Catal. 348 (2006) 2457
40. Rabalakos C., and Wulff W.D. J. Am. Chem. Soc. 130 (2008) 13524
41. Rampalakos C., and Wulff W.D. Adv. Synth. Catal. 350 (2008) 1785
42. Denmark S.E., Barsanti P.A., Wong K.-T., and Stavenger R.A. J. Org. Chem. 63 (1998) 2428
43. Denmark S.E., and Wynn T. J. Am. Chem. Soc. 123 (2001) 6199
44. Denmark S.E., and Fan Y. J. Am. Chem. Soc. 124 (2002) 4233
45. For reviews:
46. McCarthy M., and Guiry P.J. Tetrahedron 57 (2001) 3809
47. Shimizu H., Nagasaki I., and Saito T. Tetrahedron 61 (2005) 5405
48. Meisenheimer J., and Hoering M. Chem. Ber. 60 (1927) 1425
49. Gillespie K.M., Sanders C.J., O'Shaughnessy P., Westmoreland I., Thickitt C.P., and Scott P. J. Org. Chem. 67 (2002) 3450
50. Marxen T.L., Johnson B.J., Nilsson P.V., and Pignolet L.H. Inorg. Chem. 23 (1984) 4663
51. Wood M.C., Leitch D.C., Yeung C.S., Schafer J.A., and Kozak L.L. Angew. Chem., Int. Ed. 46 (2007) 354
52. During the preparation of this paper, Zhang et al presented the same diamine with the central-to-axial chirality transformation strategy, see:. Sun F., Li W., Zhou L., Zhang X. Adv. Synth. Catal. 351 (2009) 2553
53. For some reviews, see:
54. Bringmann G., Mortimer A.J.P., Keller P.A., Gresser M.J., Garner J., and Breuning M. Angew. Chem., Int. Ed. 44 (2005) 5384 For some examples, see:
55. Lin G.-Q., and Zhong M. Tetrahedron Lett. 38 (1997) 1087
56. Takashi S., Hideyuki Y., Shintaro I., and Akira T. Tetrahedron: Asymmetry 8 (1997) 649
57. Spring D.R., Krishnan S., Blackwell H.E., and Schreiber S. J. Am. Chem. Soc. 124 (2002) 1354
58. Lipshutz B.H., Kayser F., and Liu Z.-P. Angew. Chem., Int. Ed. Engl. 33 (1994) 1842
59. Lipshutz B.H., James B., Vance S., and Carrico I. Tetrahedron Lett. 38 (1997) 753
60. Miyano S., Fukushima H., Handa S., Ito H., and Hashimoto H. Bull. Chem. Soc. Jpn. 61 (1988) 3249
61. Rawal V.H., Florjancic A.S., and Singh S.P. Tetrahedron Lett. 35 (1994) 8985
62. Gorobets E.G., McDonald R., and Keay B.A. Org. Lett. 8 (2006) 1483
63. Michaud G., Bulliard M., Ricard L., Genêt J.-P., and Marinetti A. Chem.-Eur. J. 8 (2002) 3327
64. Qiu L., Kwong F.Y., Wu J., Lam W.H., Chan S., Yu W.-Y., Li Y.-M., Guo R., Zhou Z., and Chan A.S.C. J. Am. Chem. Soc. 128 (2006) 5955
65. Zhang, X. U.S. Patent 6,521,769, 2003 (filed 1999).
66. Sun X., Zhou L., Li W., and Zhang X. J. Org. Chem. 73 (2008) 1143
67. Wawzonek S., and Wang S.C. J. Org. Chem. 16 (1951) 1271
68. Kawano H., Ishii Y., Saburi M., and Uchida Y. J. Chem. Soc., Chem. Commun. (1988) 87
69. Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobayashi H., Akutagawa S., Ohta T., Takaya H., and Noyori R. J. Am. Chem. Soc. 110 (1988) 629
70. Fan Q.-H., Yeung C.-H., and Chan A.S.C. Tetrahedron: Asymmetry 8 (1997) 4041
71. Mitsunobu O. Synthesis (1981) 1
72. Kumara Swamy K.C., Bhuvan Kumar N.N., Balaraman E., and Pavan Kumar K.V.P. Chem. Rev. 109 (2009) 2551
73. Cereghetti M., Schmid R., Schoenholzer P., and Rageot A. Tetrahedron Lett. 37 (1996) 5343
74. Chen Y.-X., Chan A.S.C., Li Y.-M., and Lam K.-H. Chin. J. Chem. 19 (2001) 5343
75. 2=0.0549 for 2837 observed [I>2σ(I)] reflections. CCDC 736936 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223 336 033; or deposit@ccdc.cam.ac.uk).
76. For recent reviews, see:
77. Xie J., and Zhou Q. Acc. Chem. Res. 41 (2008) 581
78. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
79. Zhang W., Chi Y., and Zhang X. Acc. Chem. Res. 40 (2007) 1278
80. Zhao D., Wang Z., and Ding K. Tetrahedron Lett. 48 (2007) 5095
81. Liu Y., Sandoval C.A., Yamaguchi Y., Zhang X., Wang Z., Kato K., and Ding K. J. Am. Chem. Soc. 128 (2006) 14212
82. Zhao B., Wang Z., and Ding K. Adv. Synth. Catal. 348 (2006) 1049
83. Liu Y., and Ding K. J. Am. Chem. Soc. 127 (2005) 10488
84. Zhang Y.J., Wei H., and Zhang W. Tetrahedron 65 (2009) 1281
85. Wei H., Zhang Y.J., Dai Y., Zhang J., and Zhang W. Tetrahedron Lett. 49 (2008) 4106
86. Pautigny C., Jeulin S., Ayad T., Zhang Z., Genet J.-P., and Ratovelomanana-Vidal V. Adv. Synth. Catal. 350 (2008) 2525
87. Wu S., Zhang W., Zhang Z., and Zhang X. Org. Lett. 6 (2004) 3565
88. Duan Z.-C., Hu X.-P., Zhang C., Wang D.-Y., Yu S.-B., and Zheng Z. J. Org. Chem. 74 (2009) 9191
89. Wang D.-Y., Hu X.-P., Hou C.-J., Deng J., Yu S.-B., Duan Z.-C., Huang J.-D., and Zheng Z. Org. Lett. 11 (2009) 3226
90. Duan Z.-C., Hu X.-P., Deng J., Yu S.-B., Wang D.-Y., and Zheng Z. Tetrahedron: Asymmetry 20 (2009) 588
91. Wang D.-Y., Hu X.-P., Deng J., Yu S.-B., Duan Z.-C., and Zheng Z. J. Org. Chem. 74 (2009) 4408
92. Zhang B., Xu M.-H., and Lin G.-Q. Org. Lett. 11 (2009) 4712
93. Zhang F.-Y., Kwok W., and Chan A.S.C. Tetrahedron: Asymmetry 12 (2001) 2337
94. Miyano S., Nawa M., Mori A., and Hashimoto H.B. Bull. Chem. Soc. Jpn. 57 (1984) 2171
95. Chen Y.-X., Li Y.-M., Lam K.-H., and Chan A.S.C. Chin. J. Chem. 21 (2003) 66