One-pot synthesis of pentasubstituted cyclohexanes by a Michael addition followed by a tandem inter-intra double Henry reaction

Chemistry - A European Journal

Volumn 15, Issue 27, 2009, Pages 6576-6580

  Ruano, José Luis García ^a   Marcos, Vanesa ^a   Suanzes, Juan Antonio ^a   Marzo, Leyre ^a   Alemán, José ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Carbocycles; Diarylprolinol ethers; Homogeneous catalysis; One pot reactions; Organocatalysis

Indexed keywords

CARBOCYCLES; DIARYLPROLINOL ETHERS; HOMOGENEOUS CATALYSIS; ONE-POT REACTIONS; ORGANOCATALYSIS;

ALDEHYDES; CATALYSIS; COMPLEXATION; CYCLOHEXANE; ETHERS; ISOMERS; PARAFFINS; RATE CONSTANTS; REACTION KINETICS; UNSATURATED COMPOUNDS;

ADDITION REACTIONS;

EID: 67650305542     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900894     Document Type: Article

References (118)

1. For recent general reviews on domino-, multicomponent reactions, see: a)J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001;
2. b) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
3. Angew. Chem. Int. Ed. 2005, 44, 1602;
4. c) J. Zhu, H. Bien-aymé, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005;
5. d) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organ-ic Synthesis, Wiley-VCH, Weinheim, 2006;
6. e) H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362;
7. Angew. Chem. Int. Ed. 2006, 45, 354;
8. f) H. Pellissier, Tetrahedron 2006, 62, 1619;
9. g) H. Pellissier, Tetrahedron 2006, 62, 2143;
10. h) X. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037;
11. for recent examples of domino-, multicomponent reactions in organocatalysis, see: M. Lu, D. Zhu, Y. Lu, Y. Hou, B. Tan, G. Zhong, Angew. Chem. 2008, 120, 10341;
12. Angew. Chem. Int. Ed. 2008, 47, 10187;
13. i) J. Wang, F. Yu, X. Zhang, D. Ma, Org. Lett. 2008, 10, 2561;
14. j) B.-C. Hong, R. Y. Nimje, A. A. Sadani, J.-H. Liao, Org. Lett. 2008, 10, 2345;
15. k) D. Enders, C. Wang, J. W. Bats, Angew. Chem. 2008, 120, 7649;
16. Angew. Chem. Int. Ed. 2008, 47, 7539;
17. l) H. Li, L. Zu, H. Xie, J. Wang, W. Wang, Chem. Commun. 2008, 5636;
18. m) P. Kotame, B.-C. Horng, J.-H. Liao, Tetrahedron Lett. 2009, 50, 704;
19. n) L. Albrecht, B. Richter, C. Vila, H. Krawczyk, K. A. Jørgen-sen, Chem. Eur. J. 2009, 15, 3093;
20. M. Marigo, S. Bertelsen, A. Landa, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475;
21. o) B. Dhevalapally, Y. Ramachary, R. Vijayendar, K. Mamillapalli, Org. Biomol. Chem. 2008, 6, 4188;
22. p) J. Franzén, A. Fisher, Angew. Chem. 2009, 121, 1377;
23. Angew. Chem. Int. Ed. 2009, 48, 787;
24. q) Y.G. Wang, T. Kumano, T. Kano, K. Maruoka, Org. Lett. 2009, 11, 2027.
25. For recent reviews on organocatalysis, see: a) P. L. Dalko, P. L. Moisan, Angew. Chem. 2004, 116, 5248;
26. Angew. Chem. Int. Ed. 2004, 43, 5138;
27. b) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2004;
28. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
29. d) Special issue on organocatalysis: Acc. Chem. Res. 2004, 37;
30. e) B. List, J.-W. Yang, Science 2006, 313, 1584;
31. f) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. C. Vo, Drug Discovery Today 2007, 12, 8;
32. g) B. List, Chem. Commun. 2006, 819;
33. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007;
34. For general reviews of β-funtionalization, see: i) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
35. j) D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299;
36. k) C. F. Barbas III, Angew. Chem. 2008, 120, 44;
37. Angew. Chem. Int. Ed. 2008, 47, 42;
38. l) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
39. Angew. Chem. Int. Ed. 2008, 47, 4638;
40. m) P. Melchiorre, M. Marigo, A. Car-lone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
41. Angew. Chem. Int. Ed. 2008, 47, 6138.
42. For a definition and classification of tandem, cascade or one-pot re-actions, see: a) D. E. Fogg, E. N. dos Santos, Coord. Chem. Rev. 2004, 248, 2365;
43. b) C. J. Chapman, C. G. Frost, Synthesis 2007, 1.
44. a) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
45. b)D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471;
46. Angew. Chem. Int. Ed. 2007, 46, 467;
47. c) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
48. Angew. Chem. Int. Ed. 2007, 46, 1101;
49. d) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
50. Angew. Chem. Int. Ed. 2007, 46, 4922;
51. e) S. Cabrera, J. Alemán, P. Bolze, S. Bertelsen, K. A. Jørgensen, Angew. Chem. 2008, 120, 127;
52. Angew. Chem. Int. Ed. 2008, 47, 121;
53. f) E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362;
54. Angew. Chem. Int. Ed. 2007, 46, 9202;
55. g) O. Penon, A. Carlone, A. Mazzanti, M. Locatelli, L. Sambri, G. Bartoli, P. Melchiorre, Chem. Eur. J. 2008, 14, 4788.
56. a) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204;
57. Angew. Chem. Int. Ed. 2004, 43, 2152;
58. b) I. Ibrahem, A. Cordova, Angew. Chem. 2006, 118, 1986;
59. Angew. Chem. Int. Ed. 2006, 45, 1952;
60. c) V. Komanduri, M. J. Kri-sche, J. Am. Chem. Soc. 2006, 128, 16448;
61. d) S. Chercheja, P. Eil-bracht, Adv. Synth. Catal. 2007, 349, 1897;
62. e) O. Abillard, B. Breit, Adv. Synth. Catal. 2007, 349, 1891;
63. f) S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336;
64. g) W. Hu, X. Xu, J. Zhou, W.-J Liu, H. Huang, J. Hu, L. Yang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 7782;
65. h) T. Yang, A. Ferrali, L. Campbell, D. J. Dixon, Chem. Commun. 2008, 2923;
66. i) S. Chercheja, T. Rothenbücher, P. Eilbracht, Adv. Synth. Catal. 2009, 251, 339;
67. j) for examples of combinations of two organocatalysts, see: Y. Huang, A. M. Walji, C. H. Larsen, D. W. C MacMillan, J. Am. Chem. Soc. 2005, 127, 15051.
68. For the synthesis of 1,3-dihydroxy-2-nitroindane from benzene-1,2-dicarbaldehyde and nitromethane with base, see: a) J. Kocourek, M. Tichá, V. Jiráček, Angew. Chem. 1964, 6, 263;
69. Angew. Chem. Int. Ed. Engl. 1964, 3, 62;
70. for a double Henry reaction catalyzed by tetrame-thylguanidine, see: b) F. A. Luzzio, R. W. Fitch, J. Org. Chem. 1999, 64, 5485;
71. c) R. W. Fitch, F. A. Luzzio, Ultrason. Sonochem. 1997, 4, 99;
72. for an organometallic asymmetric approach to this reaction, see: d) H. Sasai, M. Horoi, Y. M. A. Yamada, M. Shibasaki, Tetrahedron. Lett. 1997, 38, 6031.
73. For a review of Henry reactions, see: a) F. A. Luzzio, Tetrahedron 2001, 57, 915;
74. for examples of the use of fluoride ions as catalysts, see: b) J. H. Clark, J. M. Miller, K.-H. So, J. Chem. Soc. Perkin Trans. 1 1978, 941 (Michael reaction);
75. c) J. L. García Ruano, M. Topp, J. López-Cantarero, J. Alemán, M. Remuiñan, M. B. Cid, Org. Lett. 2005, 7, 4407 (aza-Henry reaction).
76. For examples of Michael reactions of 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes, see: a) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
77. Angew. Chem. Int. Ed. 2006, 45, 4305;
78. b) M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 2008, 14, 6329;
79. c) P. T. Franke, B. Richter, K. A. Jørgensen, Chem. Eur. J. 2008, 14, 6317;
80. for recent examples of iminium activation, see: d) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
81. Angew. Chem. Int. Ed. 2006, 45, 4193;
82. e) H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 7007;
83. Angew. Chem. Int. Ed. 2006, 45, 6853;
84. f) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354;
85. g) Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328;
86. h) S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536;
87. i) P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029;
88. Angew. Chem. Int. Ed. 2007, 46, 1983;
89. j) D. Enders, M. H. Bonten, G. Raabe, Synlett 2007, 0885;
90. k) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588;
91. Angew. Chem. Int. Ed. 2007, 46, 4504;
92. l) I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Erikson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591;
93. Angew. Chem. Int. Ed. 2007, 46, 4507;
94. m) E. Maerten, S. Cabrera, A. Kjærsgaard, K. A. Jørgensen, J. Org. Chem. 2007, 72, 8893;
95. n) S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 12031;
96. o) S. Fustero, J. Moscardo, D. Ji-ménez, M. D. Peréz-Carrión, M. Sánchez-Roselló, C. del Pozo, Chem. Eur. J. 2008, 14, 9868;
97. p) J. Wang, A. Ma, D. Ma, Org. Lett. 2008, 10, 5425;
98. q) D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. 2008, 120, 4664;
99. Angew. Chem. Int. Ed. 2008, 47, 4588.
100. For the first application of silyldiarylprolinol ethers as catalysts, see: a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
101. Angew. Chem. Int. Ed. 2005, 44, 794;
102. see also: b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769;
103. Angew. Chem. Int. Ed. 2005, 44, 3703;
104. c) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
105. Angew. Chem. Int. Ed. 2005, 44, 4212;
106. d) J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296;
107. for a general review of the use of silyldiarylprolinol ethers as catalysts, see: e) A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922.
108. a) C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, A. Puente, S. Vera, Angew. Chem. 2007, 119, 8583;
109. Angew. Chem. Int. Ed. 2007, 46, 8431;
110. b) L. Hojabri, A. Hartikka, F. M. Moghaddam, P. I. Arvidssona, Adv. Synth. Catal. 2007, 349, 740;
111. c) H. Gotoh, H. Ishikawa, Y. Hayashi, Yujirom, Org. Lett. 2007, 9, 5307;
112. d) Y. Wang, P. Li, X. Liang, T. Zhang, J. Ye, Chem. Commun. 2008, 1232.
113. These reactions required the use of 20 mol% of fluoride source be-cause a 10 mol% was consumed by the silyl prolinol ether 4.
114. Lower yields were obtained if the reaction was performed in two consecutive reactions. Under these conditions, the Michael adduct was obtained in 80% yield, which suggests an average yield of around 75% for each one of the Henry reactions involved in the one-pot process.
115. We have tried aromatic a,β-unsaturated aldehydes under different conditions and catalysts without any conversion.
116. CCDC-718713 (7b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
117. Reactions with nitroethane afforded mixtures of diastereoisomers, which is expected because the presence of an additional methyl group on the ring distorts the ideal all-trans relationship achieved for all substituents in compounds 7, indicating that several diastereo-isomers have a similar stability.
118. To confirm this suggestion, samples of Michael adduct 5a (94% ee), which was isolated in the first step, were exposed to 40 mol% CsF. After 18 h we recovered the compound in 62% ee, demonstrating that the catalyst (CsF) initiated the retro-Michael reaction.