Thermal and Sc(OTf)3 catalyzed 1,3-dipolar cycloaddition of open-chain nitrones to α,β-unsaturated lactones: Combined experimental and computational studies

Tetrahedron Asymmetry

Volumn 24, Issue 2-3, 2013, Pages 89-103

  Śniezek, Marcin ^a   Stecko, Sebastian ^a   Panfil, Irma ^a   Furman, Bartłomiej ^a   Urbańczyk Lipkowska, Zofia ^a   Chmielewski, Marek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; MESYLIC ACID DERIVATIVE; NITRONE DERIVATIVE; SCANDIUM TRIFLUOROMETHANESULFONATE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; ELECTROPHILICITY; EXPERIMENTAL STUDY; ISOMERIZATION; MATHEMATICAL ANALYSIS; PRIORITY JOURNAL; QUANTUM MECHANICS; REACTION TIME; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 84873636395     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.12.006     Document Type: Article

References (124)

1. G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, and E. Lukevics Curr. Med. Chem. 10 2003 1744 1758
2. J.J. Tufariello Acc. Chem. Res. 12 1979 396 403
3. J.J. Tufariello, and J.P. Tette J. Org. Chem. 40 1975 3866 3869
4. S.E. Denmark, and J.J. Cottell J. Org. Chem. 66 2001 4276 4284
5. S.E. Denmark, and A.R. Hurd J. Org. Chem. 65 2000 2875 2886
6. S.E. Denmark, and A. Thorarensen J. Am. Chem. Soc. 119 1997 125 137
7. P. DeShong, C.M. Dicken, J.M. Leginus, and R.R. Whittle J. Am. Chem. Soc. 106 1984 5598 5602
8. P. DeShong, and J.M. Leginus J. Am. Chem. Soc. 105 1983 1686 1688
9. R.L. Funk, G.L. Bolton, J.U. Daggett, M.M. Hansen, and L.H.M. Horcher Tetrahedron 41 1985 3479 3495
10. A. Goti, F. Cardona, and A. Brandi Synlett 1996 761 763
11. A. Goti, S. Cicchi, M. Cacciarini, F. Cardona, V. Fedi, and A. Brandi Eur. J. Org. Chem. 2000 3633 3645
12. A. Goti, S. Cicchi, V. Fedi, L. Nannelli, and A. Brandi J. Org. Chem. 62 1997 3119 3125
13. A. Goti, V. Fedi, L. Nannelli, F. De Sarlo, and A. Brandi Synlett 1997 577 579
14. A.B. Holmes, B. Bourdin, I. Collins, E.C. Davison, A.J. Rudge, T.C. Stork, and J. Warner Pure Appl. Chem. 69 1997 531 536
15. W. Kliegel Pharmazie 32 1977 411 416
16. A.E. McCaig, K.P. Meldrum, and R.H. Wightman Tetrahedron 54 1998 9429 9446
17. M.A. Schwartz, and G.C. Swanson J. Org. Chem. 44 1979 953 958
18. J.J. Tufariello, H. Meckler, and K.P.A. Senaratne Tetrahedron 41 1985 3447 3453
19. H.E. Bays, P.B. Moore, M.A. Drehobl, S. Rosenblatt, P.D. Toth, C.A. Dujovne, R.H. Knopp, L.J. Lipka, A.P. LeBeaut, B. Yang, L.E. Mellars, C. Cuffie-Jackson, and E.P. Veltri Clin. Ther. 23 2001 1209 1230
20. D.A. Burnett, M.A. Caplen, H.R. Davis, R.E. Burrier, and J.W. Clader J. Med. Chem. 37 1994 1733 1736
21. L.-Y. Chen, A. Zaks, S. Chackalamannil, and S. Dugar J. Org. Chem. 61 1996 8341 8343
22. J.W. Clader J. Med. Chem. 47 2003 1 9
23. S. Dugar, J.W. Clader, T.-M. Chan, and H. Davis J. Med. Chem. 38 1995 4875 4877
24. Ghosal, A.; Zbaida, S.; Chowdhury, S. K.; Iannucci, R. M.; Feng, W.; Alton, K. B.; Patrick, J. E.; Davis, H. R. Pat. Appl. 2002.
25. R.H. Knopp, H. Gitter, T. Truitt, H. Bays, C.V. Manion, L.J. Lipka, A.P. LeBeaut, R. Suresh, B. Yang, and E.P. Veltri Eur. Heart J. 24 2003 729 741
26. R.S. Keri, K.M. Hosamani, H.S. Reddy, and R.V. Shingalapur Arch. Pharm. 343 2010 237 247
27. Aslanian, R. G.; Bennett, C. E.; Burnett, D. A.; Chan, T. -Y.; Kiselgof, E. Y.; Knutson, C. E.; Harris, J. M.; McKittrick, B. A.; Palani, A.; Smith, E. M.; Vaccaro, H. M.; Xiao, D.; Kim, H. M., Pat. Appl. WO 2008/033464A2, 2008.
28. I. Banik, F.F. Becker, and B.K. Banik J. Med. Chem. 46 2002 12 15
29. M.J. Meegan, M. Carr, A.J.S. Knox, D.M. Zisterer, and D.G. Lloyd J. Enzyme Inhib. Med. Chem. 23 2008 668 685
30. I. Panfil, and M. Chmielewski Tetrahedron 41 1985 4713 4716
31. I. Panfil, M. Chmielewski, and C. Bełżecki Heterocycles 24 1986 1609 1617
32. I. Panfil, C. Bełżecki, and M. Chmielewski J. Carbohydr. Chem. 6 1987 463 470
33. I. Panfil, C. Bełżecki, Z. Urbanczyk-Lipkowska, and M. Chmielewski Tetrahedron 47 1991 10087 10094
34. D. Socha, M. Jurczak, and M. Chmielewski Carbohydr. Res. 336 2001 315 318
35. I. Panfil, J. Solecka, and M. Chmielewski J. Carbohydr. Chem. 25 2006 673 684
36. K. Paśniczek, D. Socha, M. Jurczak, J. Solecka, and M. Chmielewski Can. J. Chem. 84 2006 534 539
37. D. Socha, K. Paśniczek, M. Jurczak, J. Solecka, and M. Chmielewski Carbohydr. Res. 341 2006 2005 2011
38. S. Stecko, M. Jurczak, Z. Urbańczyk-Lipkowska, J. Solecka, and M. Chmielewski Carbohydr. Res. 343 2008 2215 2220
39. S. Stecko, M. Jurczak, O. Staszewska-Krajewska, J. Solecka, and M. Chmielewski Tetrahedron 65 2009 7056 7063
40. S. Stecko, K. Paśniczek, M. Jurczak, J. Solecka, and M. Chmielewski Pol. J. Chem. 83 2009 237 243
41. S. Stecko, J. Solecka, and M. Chmielewski Carbohydr. Res. 344 2009 167 176
42. S. Stecko, K. Paśniczek, M. Jurczak, Z. Urbańczyk- Lipkowska, and M. Chmielewski Tetrahedron: Asymmetry 17 2006 68 78
43. S. Stecko, K. Paśniczek, M. Jurczak, Z. Urbańczyk- Lipkowska, and M. Chmielewski Tetrahedron: Asymmetry 18 2007 1085 1093
44. S. Stecko, K. Paśniczek, C. Michel, A. Milet, S. Perez, and M. Chmielewski Tetrahedron: Asymmetry 19 2008 2140 2148
45. S. Stecko, K. Paśniczek, C. Michel, A. Milet, S. Pérez, and M. Chmielewski Tetrahedron: Asymmetry 19 2008 1660 1669
46. S. Stecko, J. Frelek, and M. Chmielewski Tetrahedron: Asymmetry 20 2009 1778 1790
47. M. Michalak, M. Stodulski, S. Stecko, A. Mames, I. Panfil, M. Soluch, B. Furman, and M. Chmielewski J. Org. Chem. 76 2011 6931 6936
48. M. Michalak, M. Stodulski, S. Stecko, M. Woźnica, O. Staszewska-Krajewska, P. Kalicki, B. Furman, J. Frelek, and M. Chmielewski Tetrahedron 68 2012 10806 10817
49. S. Stecko, M. Michalak, M. Stodulski, Ł. Mucha, K. Parda, B. Furman, and M. Chmielewski Synthesis 44 2012 2695 2698
50. G. Descotes, and J.-C. Martin Carbohydr. Res. 56 1977 168 172
51. D. Qiu, and R.R. Schmidt Synthesis 1990 875 877
52. F. Fazio, and M.P. Schneider Tetrahedron: Asymmetry 11 2000 1869 1876
53. M. Takhi, A.A.H. Abdel-Rahman, and R.R. Schmidt Synlett 2001 427 429
54. I.A. Grigor'ev Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis 2007 John Wiley & Sons, Inc. pp 129-434
55. I. Panfil, Z. Urbańczyk-Lipkowska, and M. Chmielewski Pol. J. Chem. 79 2005 239 249
56. K.V. Gothelf, and K.A. Jørgensen Chem. Rev. 98 1998 863 910
57. K.V. Gothelf, and K.A. Jorgensen Chem. Commun. 2000 1449 1458
58. S. Kanemasa Synlett 2002 1371 1387
59. H. Pellissier Tetrahedron 63 2007 3235 3285
60. L.M. Stanley, and M.P. Sibi Chem. Rev. 108 2008 2887 2902
61. S. Kanemasa, T. Uemura, and E. Wada Tetrahedron Lett. 33 1992 7889 7892
62. S. Kanemasa, T. Tsuruoka, and E. Wada Tetrahedron Lett. 34 1993 87 90
63. S. Kanemasa, and T. Tsuruoka Chem. Lett. 24 1995 49 50
64. O. Tamura, T. Shiro, M. Ogasawara, A. Toyao, and H. Ishibashi J. Org. Chem. 70 2005 4569 4577
65. É. Frank, J. Wölfling, B. Aukszi, V. König, T.R. Schneider, and G. Schneider Tetrahedron 58 2002 6843 6849
66. X. Li, H. Takahashi, H. Ohtake, and S. Ikegami Heterocycles 59 2003 547 571
67. S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani Chem. Lett. 1997 1039 1040
68. A.I. Sanchez-Blanco, K.V. Gothelf, and K.A. Jørgensen Tetrahedron Lett. 38 1997 7923 7926
69. S. Minakata, T. Ezoe, K. Nakamura, I. Ryu, and M. Komatsu Tetrahedron Lett. 39 1998 5205 5208
70. R. Sustmann, W. Sicking, and R. Huisgen J. Am. Chem. Soc. 117 1995 9679 9685
71. J. Liu, S. Niwayama, Y. You, and K.N. Houk J. Org. Chem. 63 1998 1064 1073
72. F.P. Cossío, I. Morao, H. Jiao, and P.v.R. Schleyer J. Am. Chem. Soc. 121 1999 6737 6746
73. M. Carda, R. Portolés, J. Murga, S. Uriel, J.A. Marco, L.R. Domingo, R.J. Zaragozá, and H. Röper J. Org. Chem. 65 2000 7000 7009
74. C. Di Valentin, M. Freccero, R. Gandolfi, and A. Rastelli J. Org. Chem. 65 2000 6112 6120
75. R. Herrera, A. Nagarajan, M.A. Morales, F. Méndez, H.A. Jiménez-Vázquez, L.G. Zepeda, and J. Tamariz J. Org. Chem. 66 2001 1252 1263
76. K. Kavitha, and P. Venuvanalingam J. Chem. Soc., Perkin Trans. 2 2002 2130 2139
77. P. Merino, J.A. Mates, J. Revuelta, T. Tejero, U. Chiacchio, G. Romeo, D. Iannazzo, and R. Romeo Tetrahedron: Asymmetry 13 2002 173 190
78. P. Merino, J. Revuelta, T. Tejero, U. Chiacchio, A. Rescifina, and G. Romeo Tetrahedron 59 2003 3581 3592
79. M.J. Aurell, L.R. Domingo, P. Pérez, and R. Contreras Tetrahedron 60 2004 11503 11509
80. D.H. Ess, and K.N. Houk J. Phys. Chem. A 109 2005 9542 9553
81. S. Grimme, C. Mück-Lichtenfeld, E.-U. Würthwein, A.W. Ehlers, T.P.M. Goumans, and K. Lammertsma J. Phys. Chem. A 110 2006 2583 2586
82. P. Merino, T. Tejero, U. Chiacchio, G. Romeo, and A. Rescifina Tetrahedron 63 2007 1448 1458
83. N. Acharjee, and A. Banerji Comput. Theory Chem. 967 2011 50 58
84. Domingo, and R. Luis Eur. J. Org. Chem. 2000 2265 2272
85. J. Tanaka, and S. Kanemasa Tetrahedron 57 2001 899 905
86. L.R. Domingo, W. Benchouk, and S.M. Mekelleche Tetrahedron 63 2007 4464 4471
87. HyperChem™ Professional 7.51, H., Inc., 1115 NW 4th Street, Gainesville, FL 32601, USA.
88. A. Hocquet, and M. Langgård J. Mol. Model. 4 1998 94 112
89. A.D. Becke Phys. Rev. A 38 1988 3098 3100
90. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
91. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
92. J.A. Pople, J.S. Binkley, and R. Seeger Int. J. Quantum Chem. 10 1976 1 19
93. J.A. Pople, R. Seeger, and R. Krishnan Int. J. Quantum Chem. 11 1977 149 163
94. gaussian 09, Revision A.02; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; gaussian, Inc.: Pittsburgh, PA, 2003.
95. H.B. Schlegel J. Comput. Chem. 3 1982 214 220
96. H.B. Schlegel D.R. Yarkony, Modern Electronic Structure Theory 1994 World Scientific Singapore
97. C. Peng, and H.B. Schlegel Israel J. Chem. 33 1993 449 454
98. C. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch J. Comput. Chem. 17 1996 49 56
99. K.B. Wiberg Tetrahedron 24 1968 1083 1096
100. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
101. K. Fukui Acc. Chem. Res. 14 1981 363 368
102. M. Head-Gordon, and J.A. Pople J. Chem. Phys. 89 1988 5777 5786
103. J. Tomasi, and M. Persico Chem. Rev. 94 1994 2027 2094
104. B.Y. Simkin, and I. Sheikhet Quantum Chemical and Statistical Theory of Solutions - A Computational Approach 1995 Ellis Horwood London
105. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chem. Phys. Lett. 255 1996 327 335
106. E. Cances, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
107. V. Barone, M. Cossi, and J. Tomasi J. Comput. Chem. 19 1998 404 417
108. R.G. Parr, and R.G. Pearson J. Am. Chem. Soc. 105 1983 7512 7516
109. R.G. Parr, L.v. Szentpály, and S. Liu J. Am. Chem. Soc. 121 1999 1922 1924
110. L.R. Domingo, M.J. Aurell, P. Pérez, and R. Contreras Tetrahedron 58 2002 4417 4423
111. P.K. Chattaraj, U. Sarkar, and D.R. Roy Chem. Rev. 106 2006 2065 2091
112. P. Geerlings, F. De Proft, and W. Langenaeker Chem. Rev. 103 2003 1793 1874
113. D.H. Ess, G.O. Jones, and K.N. Houk Adv. Synth. Catal. 348 2006 2337 2361
114. P. Pérez, L.R. Domingo, M. José Aurell, and R. Contreras Tetrahedron 59 2003 3117 3125
115. L.R. Domingo, M.J. Aurell, P. Pérez, and R. Contreras J. Phys. Chem. A 106 2002 6871 6875
116. R.G. Parr, and W. Yang J. Am. Chem. Soc. 106 1984 4049 4050
117. A.E. Reed, L.A. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899 926
118. R.D. Bach, J.J.W. McDouall, H.B. Schlegel, and G.J. Wolber J. Org. Chem. 54 1989 2931 2935
119. S.M. Bachrach, and M. Liu J. Org. Chem. 57 1992 6736 6744
120. Y. Li, and K.N. Houk J. Am. Chem. Soc. 115 1993 7478 7485
121. S.M. Bachrach J. Org. Chem. 59 1994 5027 5033
122. L.R. Domingo, M. Arnó, and J. Andrés J. Am. Chem. Soc. 120 1998 1617 1618
123. I. Brüning, R. Grashey, H. Hauck, R. Huisgen, and H. Seidl Org. Synth. 46 1966 127 130
124. J.H. Näsman Org. Synth. 68 1990 162 167