Acidic ionic liquid-catalyzed homologation of the polyene chain in α,β-enals (polyenals)

Tetrahedron

Volumn 67, Issue 1, 2011, Pages 173-178

  Kryshtal, Galina V ^a   Zhdankina, Galina M ^a   Ignat'Ev, Nikolai V ^b   Schulte, Michael ^b   Zlotin, Sergei G ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b MERCK KGAA   (Germany)

Author keywords

Acetals; Enals; Ionic liquids; One pot reactions; Polyenals; Recycle

Indexed keywords

1,1 DIMETHOXY 3,7 DIMETHYLOCTA 2,6 DIENE; 10 ETHOXY 8,10 DIMETHOXY 2,6 DIMETHYLDECA 2,6 DIENE; 2 (3 ETHOXY 1,3 DIMETHOXYPROPYL) 6,6 DIMETHYL BICYCLO[3.1.1]HEPT 2 ENE; 2,2 DIMETHOXYMETHYL 6,6 DIMETHYL BICYCLO[3.1.1]HEPT 2 ENE; 2,6 DIMETHYL 8 (2,6,6 TRIMETHYLCYCLOHEX 1 ENYL)OCTA 2,4,6 TRIENAL; 3 (6,6 DIMETHYL BICYCLO[3.1.1]HEPT 2 EN 2 YL)PROP 2 ENAL; 4 METHYL 6 (2,6,6 TRIMETHYLCYCLOHEX 1 ENYL)HEXA 2,4 DIENAL; 5 (6,6 DIMETHYL BICYCLO[3.1.1]HEPT 2 EN 2 YL) 2 METHYLPENTA 2,4 DIENAL; 5 (6,6 DIMETHYL BICYCLO[3.1.1]HEPT 2 EN 2 YL)PENTA 2,4 DIENAL; 5 PHENYLPENTA 2,4 DIENAL; 5,9 DIMETHYLDECA 2,4 8 TRIENAL; 7 PHENYLHEPTA 2,4,6 TRIENAL; 9 PHENYLNONA 2,4,6,8 TETRAENAL; ALDEHYDE DERIVATIVE; ALPHA,BETA ENAL DERIVATIVE; HEXA 2,4 DIENAL(SORBIC ALDEHYDE); METHYL 4 (2 METHYL 5 OXOPENTA 1,3 DIENYL)BENZOATE; METHYL 4 (2,6 DIMETHYL 7 OXOHEPTA 1,3,5 TRIENYL)BENZOATE; OCTA 2,4,6 TRIENAL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 78649769603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.005     Document Type: Article

References (102)

1. C. Thirsk, and A. Whiting J. Chem. Soc., Perkin Trans. 1 2002 999 1023
2. E.J. Corey, D.A. Clark, G. Goto, A. Marfat, C. Mioskowski, B. Samuelsson, and S. Hammarstrom J. Am. Chem. Soc. 102 1980 1436 1439
3. R.H. Green, and P.F. Lambeth Tetrahedron 39 1983 1687 1721
4. J. Rokach, and J. Adams Acc. Chem. Res. 18 1985 87 93
5. J. Rokach, Y. Guindon, R.N. Young, J. Adams, and J.G. Atkinson The Total Synthesis of Natural Products Vol. 7 1988 John Wiley and Sons New York, NY
6. B.C. Borer, and R.J.K. Taylor Synlett 1992 117 118
7. Z.-H. Peng, Y.-L. Li, W.-L. Wu, C.-X. Liu, and Y.-L. Wu J. Chem. Soc., Perkin Trans. 1 1996 1057 1065
8. C.A. Henrick Tetrahedron 33 1977 1875 1889
9. K. Mori The Total Synthesis of Natural Products Vol. 4 1981 John Wiley and Sons New York, NY
10. K. Hemming, and R.J.K. Taylor J. Chem. Soc., Chem. Commun. 1993 1409 1410
11. R. Alvarez, M. Herrero, S. López, and A.R. de Lera Tetrahedron 54 1998 6793 6810
12. J.M. Williams, and G.J. McGarvey Tetrahedron Lett. 26 1985 4891 4894
13. K.C. Nicolaou, T.K. Chakraborty, R.A. Daines, and N.S. Simpkins J. Chem. Soc., Chem. Commun. 1986 413 416
14. G.J. McGarvey, J.M. Williams, R.N. Hiner, Y. Matsubara, and T. Oh J. Am. Chem. Soc. 108 1986 4943 4952
15. S.L. Schreiber, and M.T. Goulet J. Am. Chem. Soc. 109 1987 8120 8122
16. T. Ohtani, H. Kanda, K. Misawa, Y. Urakawa, and K. Toshima Tetrahedron Lett. 50 2009 2270 2273
17. P. Li, J. Li, F. Arikan, W. Ahlbrecht, M. Dieckmann, and D. Menche J. Org. Chem. 75 2010 2429 2444
18. O. Isler, H. Lindlar, M. Montavon, R. Ruegg, and P. Zeller Helv. Chim. Acta 39 1956 249 259
19. O. Isler, H. Gutmann, H. Lindlar, M. Montavon, R. Ruegg, G. Ryser, and P. Zeller Helv. Chim. Acta 39 1956 463 473
20. O. Isler, and P. Schudel Adv. Org. Chem. 4 1963 116 224 (Wiley Interscience Series)
21. F. Kienzle Pure Appl. Chem. 47 1976 183 190
22. H. Pfander, A. Lachenmeier, and M. Hadorn Helv. Chim. Acta 63 1980 1377 1382
23. L. Dumahel, P. Dumahel, and Y. Le Gallic Tetrahedron Lett. 34 1993 319 322
24. G. Rauchschwalbe, A. Zellner, and M. Schlosser Eur. J. Org. Chem. 20 2001 3903 3909
25. A. Valla, B. Valla, R. Le Guillou, D. Cartier, L. Dufosse, and R. Labia Helv. Chim. Acta 90 2007 512 520
26. A.T. Nielsen, and W.J. Houlihan Org. React. 16 1968 1 438
27. P.K. Mahata, O. Barum, H. Jla, and H. Junjappa Synlett 2000 1345 1347
28. W.R. Bowman, C.F. Bridge, P. Brookes, M.O. Cloonan, and D.C. Leach J. Chem. Soc., Perkin Trans. 1 2002 58 66
29. R.O. Steen, L.J. Nurkkala, S.J. Angus-Dunne, C.X. Schmitt, E.C. Constable, M.J. Riley, P.V. Bernhardt, and S.J. Dunne Eur. J. Inorg. Chem. 2008 1784 1794
30. G. Wittig, and M. Reiff Angew. Chem. 80 1968 8 15
31. Angew. Chem., Int. Ed. Engl. 7 1968 7 14
32. S. Saito, and H. Yamamoto Chem. Commun. 1997 1585 1592
33. S. Saito, M. Shiozawa, M. Ito, and H. Yamamoto J. Am. Chem. Soc. 120 1998 813 814
34. M. Bellassoued, and A. Majidi J. Org. Chem. 58 1993 2517 2522
35. M. Bellassoued, and M. Salemkour Tetrahedron Lett. 34 1993 5281 5284
36. M. Bellassoued, E. Reboul, and M. Salemkour Synth. Commun. 25 1995 3097 3108
37. M. Bellassoued, and M. Salemkour Tetrahedron 52 1996 4607 4624
38. L. Duhamel, G. Ple, and Y. Ramondenc Tetrahedron Lett. 30 1989 7377 7380
39. B. Contreras, L. Duhamel, and G. Ple Synth. Commun. 20 1990 2983 2990
40. L. Duhamel, and J.-E. Ancel Tetrahedron 48 1992 9237 9250
41. H. Maeta, and K. Suzuki Tetrahedron Lett. 34 1993 341 344
42. D. Soullez, G. Ple, and L. Duhamel J. Chem. Soc., Perkin Trans. 1 1997 1639 1645
43. M. Si-Fodil, H. Ferreira, J. Gralak, and L. Duhamel Tetrahedron Lett. 39 1998 8975 8978
44. P. Villiers, D. Soullez, Y. Ramondenc, and G. Ple Tetrahedron 55 1999 14031 14042
45. T.M. Cresp, M.V. Sargent, and P. Vogel J. Chem. Soc., Perkin Trans. 1 1974 37 41
46. H.J. Bestmann, O. Vostrowsky, H. Paulus, W. Billmann, and W. Stransky Tetrahedron Lett. 1977 121 124
47. J. Rokach, R.N. Young, M. Kakushima, C.-K. Lau, R. Seguin, R. Franette, and Y. Guindon Tetrahedron Lett. 22 1981 979 981
48. H.J. Bestmann, K. Roth, and M. Ettlinger Chem. Ber. 115 1982 161 171
49. S.R. Baker, J.R. Boot, S.E. Morgan, D.J. Osborn, W.J. Ross, and P.R. Shrubsall Tetrahedron Lett. 24 1983 4469 4472
50. I. Ernest, A. Main, and R. Menasse Tetrahedron Lett. 23 1982 167 170
51. C.W. Spangler, and R.K. McCoy Synth. Commun. 18 1988 51 60
52. D.I. Ivanova, S.V. Eremin, and V.I. Shvets Tetrahedron 52 1996 9581 9588
53. H. Takahashi, K. Fujiwara, and M. Ohta Bull. Chem. Soc. Jpn. 35 1962 1498 1500
54. W. Nagata, and Y. Hayase Tetrahedron Lett. 1968 4359 4362
55. J. Boutagy, and R. Thomas Chem. Rev. 74 1974 87 89
56. A.J. Meyers, K. Tomoika, and M.P. Fleming J. Org. Chem. 43 1978 3788 3789
57. J.-M. Nuzillard, A. Boumendjel, and G. Massiot Tetrahedron Lett. 30 1989 3779 3780
58. L. Dumahel, J. Guillemont, Y. Le Gallic, G. Ple, J.-M. Poirier, Y. Ramondenc, and P. Chabardes Tetrahedron Lett. 31 1990 3129 3132
59. N. Kann, T. Rein, B. kermark, and P. Helquist J. Org. Chem. 55 1990 5312 5323
60. A. Mohamed-Hachi, E. About-Jaudet, J.-C. Combret, and N. Collignon Synthesis 1999 1188 1192
61. Y. Wang, J. Li, Y. Wu, Y. Huang, L. Shi, and J. Yang Tetrahedron Lett. 27 1986 4583 4584
62. C. Gravier-Pelletier, J. Dumas, Y. Le Merrer, and J.C. Depezay Tetrahedron Lett. 32 1991 1165 1168
63. I.N. Nazarov, I.I. Nazarova, and I.V. Torgov Dokl. Akad. Nauk SSSR 122 1958 82 85
64. Chem. Abstr. 53 1959 1123f 11224a
65. B.M. Mikhailov, and G.S. Ter-Sarkisjan J. Ger. Chem. USSR 29 1959 2560 2565 (Engl. Transl., 2525-2529)
66. L.A. Yanovskaya Izv. Akad. Nauk SSSR, Ser. Khim. 1965 1638 1644
67. Chem. Abstr. 64 1966 3342b-3342d
68. L.A. Yanovskaya, S.S. Yufit, and V.F. Kucherov The Chemistry of Acetals 1975 Nauka Moscow [in Russian]
69. S.M. Makin Pure Appl. Chem. 47 1976 173 181
70. Reuttimann, A. Eur. Patent Appl. EP816334, 1998;
71. Reuttimann, A. Eur. Patent Appl. EP919547, 1999.
72. T. Mukaiyama, and A. Ishida Chem. Lett. 1975 319 322
73. T. Mukaiyama, and A. Ishida Chem. Lett. 1975 1201 1202
74. A. Ishida, and T. Mukaiyama Bull. Chem. Soc. Jpn. 50 1977 1161 1168
75. B.W. Domagalska, L. Syper, and K.A. Wilk Synthesis 2001 2463 2469
76. B.W. Domagalska, L. Syper, and K.A. Wilk Tetrahedron 60 2004 1931 1939
77. R.I. Hoaglin, and D.H. Hirsh J. Am. Chem. Soc. 71 1949 3468 3472
78. U. Brugger, R. Lammers, and H. Mayr J. Org. Chem. 53 1988 2920 2925
79. D. Li, F. Shi, J. Peng, S. Guo, and Y. Deng J. Org. Chem. 69 2004 3582 3585
80. H.-H. Wu, F. Yang, P. Cui, J. Tang, and M.-Y. He Tetrahedron Lett. 45 2004 4963 4965
81. N. Gupta, Sonu, G.L. Kad, and J. Singh Catal. Commun. 8 2007 1323 1328
82. Y. Wang, D. Jiang, and L. Dai Catal. Commun. 9 2008 2475 2480
83. Y. Du, and F. Tian Synth. Commun. 35 2005 2703 2708
84. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis 1st ed. 2008 Wiley-VCH GmbH & KGaA Weinheim, Germany
85. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis 2nd ed. 2008 Wiley-VCH GmbH & KGaA Weinheim, Germany
86. I. Parvulescu, and C. Hardacre Chem. Rev. 107 2007 2615 2665
87. J. Durand, E. Teuma, and M. Gómez C.R. Chimie 10 2007 152 177
88. R. Šebesta, I. Kmentová, and S. Toma Green Chem. 10 2008 484 496
89. L.P. Glushko, G.V. Kryshtal, S.A. Kogan, and L.A. Yanovskaya Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.) 26 1977 869 872
90. S.Y. Lee, Y.S. Kulkarni, B.W. Burbaum, M.I. Johnston, and B.B. Snider J. Org. Chem. 53 1988 1848 1855
91. N. Lahmar, I. Aatar, T.B. Ayed, H. Amri, and M.M. Bellassoued J. Organomet. Chem. 691 2006 3018 3026
92. R.F. Borch, A.J. Evans, and J.J. Wade J. Am. Chem. Soc. 97 1975 6282 6284
93. P. Varelis, and B.L. Johnson Aust. J. Chem. 50 1997 43 51
94. Yamatsu, I.; Suzuki, T.; Abe, S.; Inai, Y.; Suzuki, Y.; Tagaya, O. Ger. Offen. DE 3320544, 1983;
95. G.V. Kryshtal, G.M. Zhdankina, and E.P. Serebryakov Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.) 42 1993 2039 2041
96. G.V. Kryshtal, and E.P. Serebryakov Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Transl.) 44 1995 1785 1804
97. Y. Sasson, and G. Rothenberg J. Clark, D. Macquarrie, Handbook of Green Chemistry and Technology 2002 Blackwell Science Ltd. Oxford
98. O. Isler, W. Huber, A. Konco, and M. Kofler Helv. Chim. Acta 30 1947 1911 1927
99. G.V. Kryshtal, G.M. Zhdankina, and S.G. Zlotin Eur. J. Org. Chem. 2005 2822 2827
100. I.N. Nazarov, S.M. Makin, V.K. Kruptzov, and V.A. Mironov J. Ger. Chem. USSR 29 1959 106 111 (Engl. Transl., 111-116)
101. A.S.-Y. Lee, and C.-L. Cheng Tetrahedron 53 1997 14255 14262
102. A. Salzer, H. Schmalle, and S. Streiff J. Organomet. Chem. 408 1991 403 424