Organocatalytic asymmetric synthesis of functionalized 3,4-dihydropyran derivatives

Chemistry - A European Journal

Volumn 14, Issue 21, 2008, Pages 6317-6321

  Franke, Patrick T ^a   Richter, Bo ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric synthesis; Conjugate addition; Cyclization; Organocatalysis; Pyrans

Indexed keywords

ALDEHYDES;

ASYMMETRIC SYNTHESIS; CONJUGATE ADDITION; CYCLIZATION; ORGANOCATALYSIS; PYRANS;

ORGANIC COMPOUNDS; CYCLIZATION;

ASYMMETRIC SYNTHESIS; CONJUGATE ADDITION; FUNCTIONALIZED; ORGANOCATALYSIS; ORGANOCATALYTIC; PYRANS;

EID: 53849084797     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800850     Document Type: Article

References (127)

1. For recent reviews on organocatalysis see, for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
2. Angew. Chem. Int. Ed. 2004, 43, 5138;
3. b) A. Berkessel, H. Gröger. Asymmetric Organocatalysis, VCH, Weinheim (Germany), 2004;
4. c) Acc. Chem. Res. 2004, 37, Issue 8, special issue on organocatalysis;
5. d) J. Seayed, B. List. Org. Biomol. Chem. 2005, 3, 719;
6. e) B. List, J.-W. Yang, Science 2006, 313, 1584;
7. f) B. List, Chem. Commun. 2006, 819;
8. g) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. C. Vo, Drug Discovery Today 2007, 2, 8;
9. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim (Germany), 2007:
10. i) Chem. Rev. 2007, 107, Issue 12, special issue on organocatalysis;
11. j) A. Dondoni, A. Massi, Angew. Chem. 2008, 120. in press;
12. Angew. Chem. Int. Ed. 2008, 47, in press.
13. For recent reviews of α-functionalisations using enamine activation see. for example: a) J. M. Betancort, C. F. Barbas III. Org. Lett. 2001, 3, 3737:
14. b) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
15. c) G. Guillena, D.J. Ramón, Tetrahedron: Asymmetry 2006, 17, 1465:
16. d) S. Bertelsen, M. Nielsen, K. A. jørgensen. Angew. Chem. 2007, 119, 7500;
17. Angew. Chem. Int. Ed. 2007, 46, 7356. For examples see:
18. e) J. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2007, 119, 5616;
19. Angew. Chem. Int. Ed. 2007, 46, 5520;
20. f) M. Tiecco, A. Carlone, S. Sternativo, F. Marini, G. Bartoli, P. Melchiorre, Angew. Chem. 2007, 119, 7006;
21. Angew. Chem. Int. Ed. 2007, 46, 6882;
22. g) C. Palomo, S. Vera, I. Velilla, A. Mielgo, E. Gómez-Bengoa. Angew. Chem. 2007, 119, 8200;
23. Angew. Chem. Int. Ed. 2007, 46, 8054.
24. For recent reviews on conjugated additions using iminium-ion activation see, for example: a) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701:
25. b) D. Almasi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299;
26. c) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065. For examples see e.g.:
27. d) K. A. Ahrendt, C.J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
28. e) M. Marigo, J. Frenzen, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 4790;
29. f) S. Brandau, A. Landa, J. Frenzen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
30. Angew. Chem. Int. Ed. 2006, 45, 4305;
31. g) H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 4411;
32. Angew. Chem. Int. Ed. 2006, 45, 6853;
33. h) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
34. Angew. Chem. Int. Ed. 2006, 45, 4193:
35. i) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006; 128, 10354;
36. j) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 14986;
37. k) Y.K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328;
38. l) I. Ibrahem, R. Rios, J. Vesely, G. Zhao, A. Córdova, Chem. Commun. 2007, 849;
39. m) J. Vesely, I. Ibrahem, G. Zhao, R. Rios, A. Córdova. Angew. Chem. 2007, 119, 792;
40. Angew. Chem. Int. Ed. 2007, 46, 778:
41. n) S. Bertelsen, P. Diner, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536;
42. o) P. Dinér. M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029;
43. Angew. Chem. Int. Ed. 2007, 46, 1983;
44. p) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre. Angew. Chem. 2007, 119, 4588;
45. Angew. Chem. Int. Ed. 2007, 46, 45 4504;
46. q) I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Eriksson, F. Himo, A Cordova, Angew. Chem. 2007, 119, 4591;
47. Angew. Chem. Int. Ed. 2007, 46, 4507:
48. r) E. Maerten, S. Cabrera, A. Kjærsgaard, K. A. Jørgensen, J. Org. Chem. 2007, 72, 8893;
49. s) M. Rueping, E. Sugiono, E. Merino, Angew. Chem. 2008, 120, 3089;
50. Angew. Chem. Int. Ed. 2008, 47, 3046.
51. a) S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973:
52. b) B. Hong, M. Wu, H. Tseng, J. Liao, Org. Lett. 2006, 8, 2217;
53. c) B. J. Bench, C. Liu, C. R. Evett, C. M. H. Watanabe, J. Org. Chem. 2006, 71, 9458;
54. d) B.-C. Hong, M.-F. Wu, H.-C. Tseng, G.-F. Huang, C.-F. Su, J.-H. Liao, J. Org. Chem. 2007, 72, 8459;
55. e) R. M. de Figueiredo, R. Fröhlich, M. Christmann, Angew. Chem. 2008, 120, 1472;
56. Angew. Chem. Int. Ed. 2008, 47, 1450.
57. For examples see: a) M. P. Sibi, M. Hasegawa, J. Am. Chem. Soc. 2007, 129, 4124;
58. b) H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398 and references therein.
59. For nomenclature regarding multicomponent reactions, see: a) C. J. Chapman, C. G. Frost, Synthesis 2007. 1 and references herein. For recent reviews on multicomponent reactions see for example:
60. b) D. Tejedor, D. Gonzalez-Cruz, A. Santos-Expositto, J. J. Marrero-Tellado, P. de Armas, F. Garcia-Tellado, Chem. Eur. J. 2005, 11, 3502:
61. c) D.J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
62. Angew. Chem. 2005, 44, 1602;
63. d) F. Liéby-Muller, C. Simon, T. Constantieux, J. Rodriguez, QSAR Comb. Sci. 2006, 25, 432;
64. e) H. Guo, J. Ma, Angew. Chem. 2006, 118, 362:
65. Angew. Chem. Int. Ed. 2006, 45, 354;
66. f) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590:
67. Angew. Chem. Int. Ed. 2007, 46, 1570;
68. g) G. Guillena, D. J. Ramón, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693. For examples of one-pot multicomponent reactions involving conjugated addition see:
69. h) T. Bui, C.F. Barbas, III, Tetrahedron Lett. 2000, 41, 6951;
70. i) T. Iloh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett. 2003, 5, 4301;
71. j) N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292;
72. Angew. Chem. Int. Ed. 2004, 43, 1272:
73. k) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962:
74. l) J. W. Yang, M. T. Hechavarria Fonseca, B. List, J. Am. Chem. Soc. 2005, 127, 15036;
75. m) Y. Huang, A. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051:
76. n) M. Marigo, T. Schulte, J. Franzén, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710;
77. o) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765:
78. Angew. Chem. Int. Ed. 2006, 45, 3683;
79. p) M. Marigo, S. Bertelsen, A. Landa, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475:
80. q) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128. 14986;
81. r) A. Carlone, M. Marigo, C. North, A. Landa. K. A. jørgensen, Chem. Commun. 2006, 4928:
82. s) D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471:
83. Angew. Chem. Int. Ed. 2007, 46, 467;
84. t) H. Sunden, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2007, 13, 574:
85. u) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
86. Angew. Chem. Int. Ed. 2007, 46, 1101;
87. v) H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W. Wang, Org. Lett. 2007, 9, 1833;
88. w) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498;
89. x) D. Enders, A. A. Narine. T. R. Benninghaus, G. Raabe, Synlett 2007, 1667:
90. y) Y Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
91. Angew. Chem. Int. Ed. 2007, 46, 4922;
92. z) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886.
93. aa) P. T. Franke, R. L. Johansen, S. Bertelsen, K. A. Jørgensen, Chem. Asian J. 2008, 3, 216.
94. a) A. Rahman, A. Nasreen, F. Akhtar, M. S. Shekhani, J. Clardy, M. Parvez, M. I. Choudhary, J. M. A. Prod. 1997, 60, 472;
95. b) M. A. Brimble, H. Prabaharan, Tetrahedron 1998, 54, 2113:
96. c) J. C. Conway, P. Quayle, A.C. Regan, C.J. Urch, Tetrahedron 2005, 61, 11910;
97. d) R. H. Liu, W. D. Zhang, Z. B. Gu, C. Zhang, J. Su, X. K. Xu. Nat. Prod. Res. 2006, 20, 866;
98. e) E. L. Larghi, T. S. Kaufman. Synthesis 2006, 187;
99. f) Y. Tang, J. Oppenheimer, Z. Song, L. You, X. Zhang, R. P. Hsung. Tetrahedron 2006, 62, 10785:
100. g) M. Shoji, Y. Hayashi, Eur. J. Org. Chem. 2007, 3783:
101. h) E. D. Goddard-Boger, E. L. Ghisalberti, R. V. Stick, Eur. J. Org. Chem. 2007, 3925;
102. i) J. C. R. Brioche, K. M. Goodenough, D. J. Whatrup, J. P. A. Harrity, J. Org. Chem. 2008, 73, 1946;
103. j) S. Kumar, W. P. Malachowski, J. B. DuHadaway, J. M. LaLonde, P. J. Carroll, D. Jaller, R. Metz, G. C. Prendergast, A. J. Muller, J. Med. Chem. 2008, 51, 1706;
104. k) N. H. Yoo, D. S. Jang, J. L. Yoo, Y. M. Lee, Y. S. Kim, J.-H. Cho, J. S. Kim, J. Mir. Prod. 2008, 71, 713.
105. a) W. S. Emerson. G. H. Birum, R. I. Longley, J. Am. Chem. Soc. 1953, 75, 1312:
106. b) B. B. Snider, Tetrahedron Lett. 1980, 21, 1133;
107. c)M. Maier, R. R. Schmidt, Liebigs Ann. Chem. 1985, 2261;
108. d) Y. Chapleur, M.-N. Euvrard, J. Chem. Soc. Chem. Commun. 1987, 884;
109. e) R. A. John, V. Schmid, H. Wyler, Helv. Chim. Acta 1987, 70, 600;
110. f) W. H. Bunnelle, L. A. Meyer, J. Org. Chem. 1988, 53, 4038;
111. g) L. F. Tietze, H. Meier, H. Nutt, Chem. Ber. 1989, 122, 643;
112. h) H. Al-Badri, N. Collignon, J. Maddaluno, S. Masson, Chem. Commun. 2000, 1191;
113. i) A. Palasz, K. Jelska, M. Ozog, P. Serda, Monatsh. Chem. 2007, 138, 481.
114. Applications as catalysts: a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804:
115. Angew. Chem. Int. Ed. 2005, 44, 794.
116. See also: b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769:
117. Angew. Chem. Int. Ed. 2005, 44, 3703;
118. c) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284:
119. Angew. Chem. Int. Ed. 2005, 44, 4212;
120. d) J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296:
121. e) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042:
122. Angew. Chem. Int. Ed. 2006, 45, 7876.
123. Examples of similar results: a) E. Reyes, H. Jiang, A. Milelli, P. Eisner, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362:
124. Angew. Chem. Int. Ed. 2007, 46, 9202;
125. b) C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, A. Puente, S. Vera, Angew. Chem. 2007, 119, 8737;
126. Angew. Chem. Int. Ed. 2007, 46, 8583.
127. CCDC-687038 (3e) contain 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