Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide

Tetrahedron

Volumn 66, Issue 27-28, 2010, Pages 5042-5052

  Kantam, M Lakshmi ^a   Mahendar, Koosam ^a   Sreedhar, Bojja ^a   Choudary, Boyapati M ^b   Bhargava, Suresh K ^c   Priver, Steven H ^c  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b Ogene Systems I Pvt Ltd   (India)

^c RMIT UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA SULFANYL BETA AMINO ACID DERIVATIVE; AMINO ACID DERIVATIVE; ETHYL 3 [[(4 METHYLPHENYL)SULFONYL]AMINO] 2 (METHYLSULFANYL) 3 (4 NITROPHENYL)PROPANOATE; MAGNESIUM OXIDE; N SULFONYL ALDIMINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; SULFONIUM DERIVATIVE; SULFONIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MANNICH REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 77954349418     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.002     Document Type: Article

References (102)

1. T.C. Boge, and G.I. Georg E. Juaristi, Enantioselective Synthesis of β-Amino Acids 1996 Wiley-VCH New York, NY 1 and references cited therein
2. J. Tamariz E. Juaristi, Enantioselective Synthesis of β-Amino Acids 1996 Wiley-VCH New York, NY 45 and references cited therein
3. T. Iwamoto, E. Tsuji, M. Ezaki, A. Fujie, S. Hashimoto, M. Okuhara, M. Kohsaka, H. Imanaka, K. Kawabata, Y. Inamoto, and K. Sakane J. Antibiot. 43 1990 1
4. H. Ohki, Y. Inamoto, K. Kawabata, T. Kamimura, and K. Sakane J. Antibiot. 44 1991 546
5. D.H. Appela, L.A. Christianson, I.L. Karle, D.R. Powel, and S.H. Gellman J. Am. Chem. Soc. 118 1996 13071
6. D. Seebach, M. Overhand, F.N.M. Kuhnle, B. Martinoni, L. Oberer, U. Hommel, and H. Widmer Helv. Chim. Acta 79 1996 913
7. D.C. Cole Tetrahedron 50 1994 9517
8. A. Cordova Acc. Chem. Res. 37 2004 102
9. E. Juaristi, D. Quintana, and J. Escalante Aldrichimica Acta 27 1994 3
10. M. Arend, B. Westermann, and N. Risch Angew. Chem., Int. Ed. 37 1998 1044
11. S. Kobayashi, and M. Ueno E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis 2003 Springer Berlin 143 Supplement 1, Chapter 29.5
12. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069
13. S. Abele, and D. Seebach Eur. J. Org. Chem. 2000 1
14. H. Fujisawa, E. Takahashi, and T. Mukaiyama Chem. - Eur. J. 12 2006 5082
15. A.S. González, R.G. Arrayás, and J.C. Carretero Org. Lett. 8 2006 2977
16. B.C. Ranu, S. Samanta, and S.K. Guchhait Tetrahedron 58 2002 983
17. H. Fujisawa, E. Takahashi, T. Nakagawa, and T. Mukaiyama Chem. Lett. 32 2003 1036
18. J. Hernández-Toribio, R.G. Arrayás, and J.C. Carretero J. Am. Chem. Soc. 130 2008 16150
19. W.J. Chung, M. Omote, and J.T. Welch J. Org. Chem. 70 2005 7784
20. T.P. Tang, and J.A. Ellman J. Org. Chem. 67 2002 7819
21. Y. Wang, Q.F. He, H.W. Wang, X. Zhou, Z.Y. Huang, and Y. Quin J. Org. Chem. 71 2006 1588
22. M. Perisamy, S. Suresh, and S.S. Ganesan Tetrahedron Lett. 46 2005 5521
23. A.V. Sivakumar, G.S. Babu, and S.V. Bhat Tetrahedron: Asymmetry 12 2001 1095
24. S. Hata, M. Iguchi, T. Iwasawa, K. Yamada, and K. Tomioka Org. Lett. 6 2004 1721
25. S. Matsunaga, N. Kumagai, S. Harada, and M. Shibasaki J. Am. Chem. Soc. 125 2003 4712
26. S. Harada, S. Handa, S. Matsunaga, and M. Shibasaki Angew. Chem., Int. Ed. 44 2005 4365
27. A.G. Wenzel, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 12964
28. B.M. Trost, and L.M. Terrell J. Am. Chem. Soc. 125 2003 338
29. B. List, W.T. PojarlievBiller, and H.J. Martin J. Am. Chem. Soc. 124 2002 827
30. J.C. Adrian, and M.L. Snapper J. Org. Chem. 68 2003 2143
31. T. Honda, H. Wakabayashi, and K. Kanai Chem. Pharm. Bull. 50 2002 307
32. A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, N. Yasuda, H. Uekusa, T. Ono, D.O. Berbasov, and V.A. Soloshonok J. Org. Chem. 68 2003 7448
33. B. Heldreth, T.E. Long, S. Jang, G.S.K. Reddy, E. Turos, S. Dickey, and D.V. Lim Bioorg. Med. Chem. 14 2006 3775
34. S. Metayer, I. Seiliez, A. Collin, Y.M. Duchene, P.-A. Geraert, and S. Tesseraud J. Nutr. Biochem. 19 2008 207
35. D.I. Simon, M.E. Mullins, L. Jia, B. Gaston, D.J. Singel, and J.S. Stamler Proc. Natl. Acad. Sci. U.S.A. 93 1996 4736
36. M.W. Foster, T. McMahon, and J. Stamler Trends Mol. Med. 9 2003 160
37. T. Equbal, O. Silakari, G. Rambabu, and M. Ravikumar Bioorg. Med. Chem. Lett. 17 2007 1594
38. M.E. Bunnage, A.N. Chernega, S.G. Davies, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1994 1129
39. C. David, L. Bischoff, H. Meudal, A. Mothe, N. De Mota, S. Da Nascimento, C.L. Cortes, F.M.C. Zaluski, and B.P. Roques J. Med. Chem. 42 1999 5197
40. C. Anne, S. Turcaud, J. Quancard, F. Teff, H. Meudal, F.M.C. Zaluski, and B.P. Roques J. Med. Chem. 46 2003 4648
41. C. Anne, A. Blommaert, S. Turcaud, A.S. Martin, H. Meudal, and B.P. Roques Bioorg. Med. Chem. 11 2003 4655
42. A. Blommaert, S. Turcaud, C. Anne, and B.P. Roques Bioorg. Med. Chem. 12 2004 3055
43. C. Anne, S. Turcaud, A.G.S. Blommaert, F. Darchen, E.A. Johnson, and B.P. Roques ChemBioChem. 6 2005 1375
44. B.A. McKittrick, K. Ma, K. Huie, N. Yumibe, H. Davis Jr., J.W. Clader, and M. Czarniecki J. Med. Chem. 41 1998 752
45. M.A. Ondetti, D.W. Cushman, and B. Rubin Science 196 1977 441
46. D.W. Cushman, H.S. Cheung, E.F. Sabo, and M.A. Ondetti Biochemistry 16 1977 5484
47. M. Shimazaki, J. Hasegawa, K. Kan, K. Nomura, Y. Nose, H. Kondo, T. Ohashi, and K.M. Watanabe Chem. Pharm. Bull. 30 1982 3139
48. J.I.C. Lena, S.G. Davies, P.M. Roberts, B. Roux, A.J. Russell, E.M.S. Fernandez, and A.D. Smith Tetrahedron: Asymmetry 17 2006 1135
49. V.K. Aggarwal, J.P.H. Charmant, C. Ciampi, J.M. Hornby, C.J. O'Brien, G. Hynd, and R. Parsons J. Chem. Soc., Perkin Trans. 1 2001 3159
50. Y. Arroyo, A. Meana, J.F. Rodriguez, M. Santos, M.A. Sanz-Tejedor, and J.L. Garcia-Ruano J. Org. Chem. 70 2005 3914
51. M.D. Paolis, J. Blankenstein, M. Bois-Choussy, and J. Zhu Org. Lett. 4 2002 1235
52. H. Ohkura, M. Handa, T. Katagiri, and K. Uneyama J. Org. Chem. 67 2002 2692
53. T.H. Chuang, and K.B. Sharpless Org. Lett. 2 2000 3555
54. N. Azizi, L. Torkiyan, and M.R. Saidi Org. Lett. 8 2006 2079
55. M. Kidwai, N.K. Mishra, V. Bansal, A. Kumar, and S. Mozumdar Tetrahedron Lett. 50 2009 1355
56. E. Lucas, S. Decker, A. Khaleel, A. Seitz, S. Fultz, A. Ponce, W. Li, C. Carnes, and K.J. Klabunde Chem. - Eur. J. 7 2001 2505
57. R. Schlogl, and S.B. Abd Hamid Angew. Chem., Int. Ed. 43 2004 1628
58. A.T. Bell Science 299 2003 1688
59. C.L. Carnes, and K.J. Klabunde Langmuir 16 2000 3764
60. K.J. Klabunde, and R.S. Mulukutla Nanoscale Materials in Chemistry 2001 Wiley Interscience New York, NY Chapter 7, p 223
61. B.M. Choudary, M.L. Kantam, K.V.S. Ranganath, K. Mahendar, and B. Sreedhar J. Am. Chem. Soc. 126 2004 3396
62. B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, and B. Sreedhar J. Am. Chem. Soc. 127 2005 13167
63. B.M. Choudary, K. Mahendar, and K.V.S. Ranganath J. Mol. Catal. A: Chem. 234 2005 25
64. B.M. Choudary, K. Mahendar, M.L. Kantam, K.V.S. Ranganath, and T. Athar Adv. Synth. Catal. 348 2006 1977
65. M.L. Kantam, K.V.S. Ranganath, K. Mahendar, L. Chakrapani, and B.M. Choudary Tetrahedron Lett. 48 2007 7646
66. M.L. Kantam, K. Mahendar, B. Sreedhar, and B.M. Choudary Tetrahedron 64 2008 3351
67. M.L. Kantam, K. Mahendar, B. Sreedhar, K.V. Kumar, and B.M. Choudary Synth. Commun. 38 2008 3919
68. B.E. Love, S.P. Raje, and T.C. Williams II Synlett 1994 493
69. W.B. Jennings, and C.J. Lovely Tetrahedron Lett. 29 1988 3725
70. F. Chemla, V. Hebbe, and J. Normant Synthesis 2000 75
71. G. Liu, D.A. Cogan, T.D. Owens, T.P. Tang, and J.A. Ellman J. Org. Chem. 64 1999 1278
72. J.G. Ruano, J. Aleman, M.B. Cid, and A. Parra Org. Lett. 7 2005 179
73. X.-F. Yang, M.-J. Zhang, X.-L. Hou, and L.-X. Dai J. Org. Chem. 67 2002 8097
74. A.-H. Li, Y.-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia, and L. Lin J. Org. Chem. 63 1998 4338
75. D.-K. Wang, L.-X. Dai, and X.-L. Hou Chem. Commun. 1997 1231
76. A.-H. Li, L.-X. Dai, X.-L. Hou, and M.-B. Chen J. Org. Chem. 61 1996 4641
77. Y.-G. Zhou, A.-H. Li, X.-L. Hou, and L.-X. Dai Tetrahedron Lett. 38 1997 7225
78. A.J. Speziale, C.C. Tung, K.W. Ratts, and A. Yao J. Am. Chem. Soc. 87 1965 3460
79. Crystal structure and refinement data for compound ethyl-3-{[(4- methylphenyl)sulfonyl]amino}-2-(methylsulfanyl)-3-(4-nitrophenyl)propanoate (major isomer) (Table 3, entry 3) is available in Supplementary data. The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 701498.
80. f values are larger for the anti isomer.
81. T. Mecozzi, M. Petrini, and R. Profeta J. Org. Chem. 66 2001 8264
82. B. Choucair, H. Leon, M.-A. Mire, C. Lebreton, and P. Mosset Org. Lett. 2 2000 1851
83. B.M. Trost, J. Jaratjaroonphong, and V. Reutrakul J. Am. Chem. Soc. 128 2006 2778
84. S. Kobayashi, T. Hamada, and K. Manabe J. Am. Chem. Soc. 124 2002 5640
85. T. Ollevier, and E. Nadeau J. Org. Chem. 69 2004 9292
86. F.A. Davis, M.B. Nolt, Y. Wu, K.R. Prasad, D. Li, B. Yang, K. Bowen, S.H. Lee, and J.H. Eardley J. Org. Chem. 70 2005 2184
87. R. Robiette J. Org. Chem. 71 2006 2726
88. D. Morton, D. Pearson, R.A. Field, and R.A. Stockman Org. Lett. 6 2004 2377
89. B.E. Maryanoff, A.B. Reitz, and B.A. Duhl-Emswiler J. Am. Chem. Soc. 107 1985 217
90. B.E. Maryanoff, A.B. Reitz, M.S. Mutter, R.R. Inners, H.R. Almond Jr., R.R. Whittle, and R.A. Olofson J. Am. Chem. Soc. 108 1986 7664
91. N.E. Shevchenko, A.S. Karpov, E.P. Zakurdaev, V.G. Nenajdenko, and E.S. Balenkova Chem. Heterocycl. Compd. 36 2000 137
92. V.G. Nenajdenko, P.V. Vertelezkij, I.D. Gridnev, N.E. Shevchenko, and E.S. Balenkova Tetrahedron 53 1997 8173
93. L. Wang, and T.K. Green Chin. J. Org. Chem. 16 1996 512
94. P. Jeevanandam, and K.J. Klabunde Langmuir 18 2002 5309
95. R. Richards, W. Li, S. Decker, C. Davidson, O. Koper, V. Zaikovski, A. Volodin, T. Rieker, and K.J. Klabunde J. Am. Chem. Soc. 122 2000 4921
96. S. Utamapanya, K.J. Klabunde, and J.R. Schlup Chem. Mater. 3 1991 175
97. K.J. Klabunde, J. Stark, O. Koper, C. Mohs, D.G. Park, S. Decker, Y. Jiang, I. Lagadic, and D. Zhang J. Phys. Chem. 100 1996 12142
98. B.M. Choudary, R.S. Mulukutla, and K.J. Klabunde J. Am. Chem. Soc. 125 2003 2020
99. D.H. Paull, C.J. Abraham, M.T. Scerba, E. Alden-Danforth, and T. Lectka Acc. Chem. Res. 41 2008 655
100. M. Shibasaki, M. Kanai, and K. Funabashi Chem. Commun. 2002 1989
101. M. Hatano, T. Maki, K. Moriyama, M. Arinobe, and K. Ishihara J. Am. Chem. Soc. 130 2008 16858
102. M. Sugita, A. Yamaguchi, N. Yamagiwa, S. Handa, S. Matsunaga, and M. Shibasaki Org. Lett. 7 2005 5339