N-Carbamate α-aminoalkyl-p-tolylsulfones - Convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9840-9848

  Błaszczyk, Roman ^a   Gajda, Anna ^a   Zawadzki, Stefan ^a   Czubacka, Ewelina ^a   Gajda, Tadeusz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Amido sulfones; 1,2 Diaminoalkanephosphonates; Aminonitrophosphonates; Aza Henry reaction; Diethyl nitromethanephosphonate; PTC reaction

Indexed keywords

CARBAMIC ACID DERIVATIVE; CINCHONA ALKALOID; IMINE; PHOSPHONIC ACID DERIVATIVE; SULFONE DERIVATIVE; SYN 2 AMINO 1 NITROALKANEPHOSPHONATE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MANNICH REACTION; MOLECULAR STABILITY; NONHUMAN; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

CINCHONA;

EID: 78649676666     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.072     Document Type: Article

References (115)

1. For recent reviews, see:
2. M. Shibasaki, and M. Kanai Chem. Pharm. Bull. 49 2001 511
3. B. Westermann Angew. Chem., Int. Ed. 42 2003 151
4. T. Vilaivan, W. Bhanthumnavin, and Y. Sritana-Anant Curr. Org. Chem. 9 2005 1315
5. M. Petrini, and E. Torregani Synthesis 2007 159
6. A. Ting, and S.E. Schaus Eur. J. Org. Chem. 2007 5797
7. E. Marqués-López, P. Merino, T. Tejero, and R.P. Herrera Eur. J. Org. Chem. 2009 2401
8. R.G. Arrayás, and J.C. Carretero Chem. Soc. Rev. 38 2009 1940
9. For recent examples, of the aza-Henry reaction using chiral betaine and guanidine catalysts, see:
10. D. Uraguchi, K. Koshimoto, and T. Ooi J. Am. Chem. Soc. 130 2008 10878
11. H.M. Lovick, and F.E. Michael Tetrahedron Lett. 50 2009 1016
12. For recent examples, of the aza-Henry reaction using chiral Lewis acids and chiral proton catalysts, see:
13. N. Nishiwaki, A.S. Gothelf, R. Knudsen, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 2992
14. N. Nishiwaki, A.S. Gothelf, R. Knudsen, T. Risgaard, and K. Jørgensen J. Am. Chem. Soc. 123 2001 5843
15. K.R. Knudsen, and K.A. Jørgensen Org. Biomol. Chem. 3 2005 1362
16. A.M. Lee, W. Kim, J. Lee, T. Hyeon, and B.M. Kim Tetrahedron: Asymmetry 15 2004 2595
17. C. Palomo, M. Oiarbide, R. Halder, A. Laso, and R. López Angew. Chem., Int. Ed. 45 2006 117
18. B.M. Trost, and D.W. Lupton Org. Lett. 9 2007 2023
19. F. Gao, J. Zhu, Y. Tang, M. Deng, and C. Qian Chirality 18 2006 741
20. J.C. Anderson, A.J. Blake, G.P. Howell, and C. Wilson J. Org. Chem. 70 2005 549
21. J.C. Anderson, G.P. Howell, R.M. Lawrence, and C.S. Wilson J. Org. Chem. 70 2005 5665
22. H. Zhou, D. Peng, B. Qin, Z. Hou, X. Liu, and X. Feng J. Org. Chem. 72 2007 10302
23. B.M. Nugent, R.A. Yoder, and J.N. Johnston J. Am. Chem. Soc. 126 2004 3418
24. A. Singh, R.A. Yoder, B. Shen, and J.N. Johnston J. Am. Chem. Soc. 129 2007 3466
25. B. Shen, and J.N. Johnston Org. Lett. 10 2008 4397
26. A. Singh, and J.N. Johnston J. Am. Chem. Soc. 130 2008 5866
27. M. Rueping, and A.P. Antonchick Org. Lett. 10 2008 1731
28. T.A. Davis, J.C. Wilt, and J.N. Johnston J. Am. Chem. Soc. 132 2010 2880
29. A.S. Hess, R.A. Yoder, and J.N. Johnston Synlett 2006 147
30. For recent examples, of the aza-Henry reaction using chiral thioureas catalysts, see:
31. T.P. Yoon, and E.N. Jacobsen Angew. Chem., Int. Ed. 44 2005 466
32. X. Xu, T. Furukawa, T. Okino, H. Miyabe, and Y. Takemoto Chem. - Eur. J. 12 2006 466
33. B. Han, Q.-P. Liu, R. Li, X. Tian, X.-F. Xiong, J.-G. Deng, and Y.-C. Chen Chem. - Eur. J. 14 2008 8094
34. C. Wang, Z. Zhou, and C. Tang Org. Lett. 10 2008 1707
35. C. Wang, X. Dong, Z. Zhang, Z. Xue, and H. Teng J. Am. Chem. Soc. 130 2008 8606
36. K. Takada, and K. Nagasawa Adv. Synth. Catal. 351 2009 345
37. T. Okino, S. Nakamura, T. Furukawa, and Y. Takemoto Org. Lett. 6 2004 625
38. M.T. Robak, M. Trincado, and J.A. Ellman J. Am. Chem. Soc. 129 2007 15110
39. X. Jiang, Y. Zhang, L. Wu, G. Zhang, X. Liu, H. Zhang, D. Fu, and R. Wang Adv. Synth. Catal. 351 2009 2096
40. C. Rampalakos, and W.D. Wulff Adv. Synth. Catal. 350 2008 1785
41. Y. Chang, J. Yang, Y. Dang, and Y. Xue Synlett 2007 2283
42. For recent examples, of the aza-Henry reaction using cinchona alkaloids catalysts, see:
43. C. Palomo, M. Oiarbide, A. Laso, and R. López J. Am. Chem. Soc. 127 2005 17622
44. F. Fini, V. Sgarzani, D. Pettersen, R.P. Herrera, L. Bernardi, and A. Ricci Angew. Chem., Int. Ed. 44 2005 7975
45. L. Bernardi, F. Fini, R.P. Herrera, A. Ricci, and V. Sgarzani Tetrahedron 62 2006 375
46. E. Gomez-Bengoa, A. Linden, R. López, I. Múgica-Mendiola, M. Oiarbide, and C. Palomo J. Am. Chem. Soc. 130 2008 7955
47. C.M. Bode, A. Ting, and S.E. Schaus Tetrahedron 62 2006 11499
48. For recent examples of the aza-Henry reaction using heterobimetallic catalysts, see:
49. K. Yamada, G. Moll, and M. Shibasaki Synlett 2001 980
50. S. Handa, V. Gnanadesikan, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 132 2010 4925
51. K. Yamada, S.J. Harwood, H. Gröger, and M. Shibasaki Angew. Chem., Int. Ed. 38 1999 3504
52. S. Handa, V. Gnanadesikan, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 129 2007 4900
53. Z. Chen, H. Morimoto, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 130 2008 2170
54. For application of N-formyl and N-Carbamate protected α-aminoalkyl-arylsulfones in the aza-Henry reaction, see:
55. R. Ballini, and M. Petrini Tetrahedron Lett. 40 1999 4449
56. M. Petrini, and E. Torregiani Tetrahedron Lett. 47 2006 3501
57. E. Foresti, G. Palmieri, M. Petrini, and M. Profeta Org. Biomol. Chem. 1 2003 4275
58. T. Nagano, and H. Kinoshita Bull. Soc. Chem. Jpn. 73 2000 1605
59. Y. Shiraishi, H. Yamauchi, T. Takamura, and H. Kinoshita Bull. Soc. Chem. Jpn. 77 2004 2219
60. Refs. 4i,5a,b,d.
61. H. Adams, J.C. Anderson, S. Peace, and A.M.K. Pennell J. Org. Chem. 63 1998 9932
62. For a recent review on the synthesis of α,β-diamino acids, see: A. Viso, R.F. de la Pradilla, A. Garcia, and A. Flores Chem. Rev. 105 2005 3167
63. J.C. Wilt, M. Pink, and J.N. Johnston Chem. Commun. 2008 4177
64. G.M. Baranov, and V.V. Perekalin Russ. Chem. Rev. 61 1992 1220
65. K.A. Petrov, V.A. Chauzov, N.N. Bogdanov, and S.V. Agafonov Zh. Obshch. Khim. 49 1979 90
66. K.A. Petrov, V.A. Chauzov, N.N. Bogdanov, and I.V. Pastukhova J. Gen. Chem. USSR 46 1976 1230
67. For recent review, see: M. Petrini Chem. Rev. 105 2005 3949
68. For the synthesis of N-Boc and N-Cbz protected α-amido sulfones, see:
69. J.B.F.N. Engeberts, and J. Strating Recl. Trav. Chim. Pays-Bas 83 1964 733
70. W.H. Pearson, A.C. Lindbeck, and J.W. Kampf J. Am. Chem. Soc. 115 1993 2623
71. A.M. Kanazawa, J.-N. Denis, and A.E. Greene J. Org. Chem. 59 1994 1238
72. T. Mecozzi, and M. Petrini J. Org. Chem. 64 1999 8970
73. J.A. Murry, D.E. Frantz, A. Soheili, R. Tillyer, E.J. Grabowski, and P. Reider J. Am. Chem. Soc. 123 2001 9696
74. E. Bernacka, A. Klepacz, and A. Zwierzak Tetrahedron Lett. 42 2001 5093
75. A. Klepacz, and A. Zwierzak Tetrahedron Lett. 43 2002 1079
76. For direct conversion of N-carbamate protected α-amido sulfones into N-carbamate imines, see:
77. J. Song, Y. Wang, and L. Deng J. Am. Chem. Soc. 128 2006 6048
78. B.M. Trost, J. Jaratjaroonphong, and V. Reutrakul J. Am. Chem. Soc. 128 2006 2778
79. A.G. Wenzel, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 12964
80. For recent reviews on asymmetric PTC, see:
81. D. Albanese Mini-Rev. Org. Chem. 3 2006 195
82. T. Hashimoto, and K. Maruoka Chem. Rev. 107 2007 5656
83. T. Ooi, and K. Maruoka Angew. Chem., Int. Ed. 46 2007 4222
84. K. Maruoka Org. Process Res. Dev. 12 2008 679
85. S. Jew, and H. Park Chem. Soc. Rev. 2009 7090
86. J. Zon Synthesis 1984 661
87. B. Lejczak, P. Kafarski, and J. Zygmunt Biochemistry 28 1989 3549
88. F. Palacios, C. Alonso, and J. De Los Santos Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs E. Juaristi, V.A. Soloshonok, Enantioselective synthesis of β-amino acids 2005 John Wiley Hoboken, NJ 292 294
89. For recent syntheses of 1,2-diaminophosphonates, see:
90. J. Zygmunt Tetrahedron 41 1985 4979
91. E.K. Dolence, and J.B. Roylance Tetrahedron: Asymmetry 15 2004 3307
92. B.-F. Li, M.-J. Zhang, X.-L. Hou, and L.-X. Dai J. Org. Chem. 67 2002 2902
93. D.G. Piotrowska, and A. Wróblewski Tetrahedron 59 2003 8405
94. E.K. Dolence, G. Mayer, and B.D. Kelly Tetrahedron: Asymmetry 16 2005 1583
95. C. De Risi, A. Dondoni, D. Perrone, and G.P. Pollini Tetrahedron Lett. 42 2001 3033
96. C. De Risi, D. Perrone, A. Dondoni, G.P. Pollini, and V. Bertolasi Eur. J. Org. Chem. 2003 1904
97. A. Studer, and D. Seebach Heterocycles 40 1995 357
98. M.M. Campbell, and N. Carruthers J. Chem. Soc., Chem. Commun. 1980 730
99. M.M. Campbell, N.I. Carruthers, and S.J. Mickel Tetrahedron 38 1982 2513
100. R. Błaszczyk, and T. Gajda Tetrahedron Lett. 48 2007 5859
101. N. Louaisil, N. Rabasso, and A. Fadel Synthesis 2007 289
102. S. Kobayashi, R. Yazaki, K. Seki, and Y. Yamashita Angew. Chem., Int. Ed. 47 2008 5613
103. R.D. Momo, F. Fini, L. Bernardi, and A. Ricci Adv. Synth. Catal. 351 2009 2283
104. A. Nose, and T. Kudo Chem. Pharm. Bull. 29 1981 1159
105. Y. Sohtome, Y. Hashimoto, and K. Nagasawa Eur. J. Org. Chem. 2006 2894
106. K. Takada, N. Takemura, K. Cho, Y. Sohtome, and K. Nagasawa Tetrahedron Lett. 48 2008 1623
107. A. Nudelman, D. Marcovici-Mizrahi, A. Nudelman, D. Flint, and V. Wittenbach Tetrahedron 60 2004 1731
108. M. Makowski, B. Rzeszotarska, L. Smelka, and Z. Kubica Liebigs Ann. Chem. 1985 775
109. S.G. Davies, G.B. Evans, and S. Pearce Tetrahedron 50 1994 7521
110. K. Błaewska, and T. Gajda Tetrahedron: Asymmetry 13 2002 671
111. N. Kazuo, Y. Shinji, A. Takao, and I. Keiichi Synth. Commun. 20 1990 2033
112. K. Błaewska, P. Paneth, and T. Gajda J. Org. Chem. 72 2007 878
113. K.D. Błaewska, and T. Gajda Tetrahedron: Asymmetry 20 2009 1337
114. B. Vakulya, S. Varga, A. Csámpai, and T. Soós Org. Lett. 7 2005 1967
115. For a recent paper on the absolute configuration determination of vicinal-diamines using NMR spectroscopy and O-methyl mandelic acid as CDA, see: Ref. 6b.